Category: 4531-54-8

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, International Journal of Pharmaceutical Sciences and Research called Development and validation of stability – indicating RP-HPLC chromatographic method by forced degradation studies for azathioprine by related substances, Author is Hiralben, S. Mehta; Shinghvi, Indrajeet; Raj, Hasumati A., which mentions a compound: 4531-54-8, SMILESS is NC1=C([N+]([O-])=O)N=CN1C, Molecular C4H6N4O2, Synthetic Route of C4H6N4O2.

Simple, rapid and reproducible stability-indicating methods were established for quant. determination of azathioprine using a, phenomenex 250 mm × 4.9 mm C18, 5 μm, inertsil and UV detection at 240 nm. The isocratic elution was used to quantify the analyte and the mobile phase was acetate buffer: acetonitrile: methanol (30: 35: 35) was pumped at 1.0 mL/min. The method was linear between 10-300 μg/mL, statistically validated for its linearity, precision and accuracy. In this study, degradation behavior of azathioprine was studied by subjecting the drug to various ICH stress conditions. The intra and inter day variation was found to be less than 1% showing high precision of the assay method. It was found that the excipients in the com. tablet did not interfere with the method. Developed method can routinely use for the estimation of azathioprine related compounds from the dosage form and also for stability sample.

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Thiomorpholine – Wikipedia,
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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Formation of 4(5)-aminoglyoxalines. I》. Authors are Balaban, Isidore E..The article about the compound:1-Methyl-4-nitro-1H-imidazol-5-aminecas:4531-54-8,SMILESS:NC1=C([N+]([O-])=O)N=CN1C).Safety of 1-Methyl-4-nitro-1H-imidazol-5-amine. Through the article, more information about this compound (cas:4531-54-8) is conveyed.

The only evidence at present that 4(5)-aminoglyoxalines are true aromatic amines is the formation, after diazotization, of colored soln with aqueous β-C10H7ONa. Reduction of 4(5)-nitro-2-methyl- and 4(5)-nitroglyoxalines with Fe and H2O, FeSO4 and NaOH, Na2S or activated Al gave no basic material. Et glyoxaline-4(5)-carboxylate and N2H4.H2O, heated on the H2O bath for 30 min., give nearly quant. glyoxaline-4(5)-carboxyhydrazide, crystallizing with 1H2O, m. 213°, reduces NH4OH-AgNO3 slowly but not Fehling solution; picrate, yellow, m. 223° (decomposition), crystallizes from 85 parts boiling H2O. With HNO3 there results glyoxaline-4(5)-carboxyazide (I), decomposes explosively at 137°; heating with H2O does not give the urea; the green solution gives an amorphous picrate, chars 230°. Boiling I with absolute EtOH for 4 hrs. gives 42.2% of 4(5)-carbethoxyaminoglyoxaline, m. 180°; picrate, golden, decomposes 210°, crystallizes from 60 parts boiling H2O; nitrate (II), decomposes 143°. I and MeOH give 50% of the corresponding carbomethoxy derivative, m. 175°; picrate, decomposes 243°. Neither derivative could be hydrolyzed by acid or alkali. II and concentrated H2SO4 give 58% of 5(4)-nitro-4(5)-carbethoxyaminoglyoxaline, m. 234° (decomposition); this could not be converted by 10% Na2CO3 into the corresponding amine. 5-Chloro-4-nitro-1-methylglyoxaline and EtOH-NH3, heated 4 hrs. at 140°, give 63.7% of the 5-NH2 derivative, yellow, m. 303° (decomposition), crystallizes from 170 parts boiling H2O; it does not form an Ac derivative, a benzylidene derivative or a picrate; after treatment with HNO2, alk. C10H7ONa gives a greenish blue color and alk. m-C6H4(OH)2 a violet color. With 16% HCl, HNO2 is liberated and α-methylamino-α-hydroxyacetamide, pale brown, m. 140°, is formed.

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Diimidazoles. IV. Derivatives of 4,5-diaminoimidazole and their attempted cyclization》. Authors are Schubert, Hermann; Heydenhauss, Dieter.The article about the compound:1-Methyl-4-nitro-1H-imidazol-5-aminecas:4531-54-8,SMILESS:NC1=C([N+]([O-])=O)N=CN1C).Application In Synthesis of 1-Methyl-4-nitro-1H-imidazol-5-amine. Through the article, more information about this compound (cas:4531-54-8) is conveyed.

The preparation of a series of 1-methyl-4-nitro-5-alkylaminoimidazoles (I) is described. The catalytic hydrogenation of I and of 1-methyl-4-nitro-5-aminoimidazole (Ia) (R = H) (II) yielded unstable diamines which could neither be isolated nor cyclized. Acetylation of II gave the di-Ac derivative (III) of II. I were formylated and acetylated smoothly; hydrogenation of the products yielded stable acyl derivatives of 4,5-diaminoimidazole. (CONHMe)2 with PCl5 gave 40.8% 5-chloro-1-methylimidazole (IV), b15 90°. IV (103 g.), 100 cc. concentrated HNO3, and 400 cc. H2O evaporated, the residue added in portions at 10° to 3 times its weight of concentrated H2SO4, and the mixture heated 2 hrs. on a water bath yielded 122 g. 5-Cl analog (V) of II, m. 149-50°. V (13.2g.)in 3.5%absolute NH3EtOH heated 2 hrs. at 130-40° in a sealed tube yielded 6.3 g. II, m. 303° (decomposition) (H2O). II (5 g.) and 200 cc. Ac2O refluxed about 5 hrs. gave 5.2 g. III, m. 149.5-50.5°. V (1.62 g.) in 25 cc. 7% absolute alc. MeNH2 refluxed 3 hrs. yielded 1.45 g. Ia (R = Me) (VI), m. 156-7° (EtOH). VI (5 g.) in 50 cc. HCO2Ac kept 20 hrs. at room temperature and concentrated yielded 5 g. the N-CHO derivative (VII), m. 142.5-3.5° (EtOH). VI (10 g.) in 200 cc. Ac2O heated 1 hr. at 90-100° gave 8.2 g. the N-Ac derivative (VIII), m. 168-9° (BuOH or dioxane). V (1.62 g.) in 37 cc. 7% absolute alc. EtNH2 refluxed 3 hrs. and refrigerated overnight yielded 1.6 g. Ia (R = Et), m. 161-2° (dioxane). In the same manner were prepared the following Ia (R, m.p., and % yield given): Pr, 114-18° (dioxan-epetr. ether), 92; Bu, 101-6° (dioxane-petr. ether), 61; PhCH2, 132-3° (EtOH), 90. Also prepared was the N-Me derivative of VI, m. 94-5.5° (C6H6-petr. ether), 47% yield. II (0.76 g.) in 30 cc. 85% HCO2H hydrogenated 4 hrs. at 17°/756 mm. over 0.2 g. PtO2 yielded a black-brown oil, which treated with dilute aqueous NaOH liberated NH3. III (0.5 g.) in 45 cc. absolute BuOH hydrogenated 40 min. at 17°/770 mm. over 0.2 g. PtO2, and the resulting oily product in C6H6 treated with the stoichiometric amount picric acid yielded 1-methyl-4-amino-5-(N,N-diacetylamino)imidazole picrate, m. 160-1° (decomposition) (BuOH). The BuOH solution from a duplicate run refluxed 1.5 hrs. under argon gave only a brown, flocculent precipitate Hydrogenation of 0.5 g. VI in H2O, dilute HCl, dry dioxane, AcOH, AcOH-HCl, and Ac2O over 0.2 g. PtO2 gave only oily unstable materials. VII (0.6 g.) in 100 cc. Bu0H hydrogenated 50 min. at 18°/763 mm., and the resulting yellow oil treated in EtOH with picric acid gave the picrate of 1-methyl-4-amino-5-(N-methyl-N-formylamino)imidazole (IX), m. 173-70 (decomposition) (H2O); styphnate m. 177-8.5° (decomposition) (H2O). The BuOH solution of the crude IX refluxed 2 hrs. under argon yielded a brown, flocculent precipitate VIII (2 g.) in 120 cc. BuOH hydrogenated 1 hr. at 20°/755 mm. over 0.4 g. PtO2 yielded 1.4 g. 5-AcMeN analog (X) of IX, m. 165-6° ( PhCl); picrate m. 217-21° (decomposition) (H2O); styphnate m. 196-9° (decomposition) (H2O); HCl salt m. 225-6° (decomposition). All attempted cyclizations of X were unsuccessful. X (0.5 g.) in 3 cc. absolute HCO2H refluxed 1.5 hrs. yielded 0.4 g. 1-methyl-4-formyl-amino-5-(N-methyl-N-acetylamino)imidazole (XI), m. 154-5.5° (absolute EtOH-Et2O). X (2.1 g.) in 15 cc. AcOH refluxed 0.5 hr. yielded 1.47 g. 4-AcNH analog of XI, m. 188.5-9.5° (1:1 dioxane-PhCl); picrate m. 166-9° (EtOH); all attempted cyclizations were unsuccessful.

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Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem

Formula: C4H6N4O2. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 1-Methyl-4-nitro-1H-imidazol-5-amine, is researched, Molecular C4H6N4O2, CAS is 4531-54-8, about Development of a HPLC-DAD stability-indicating method and compatibility study of azathioprine and folic acid as a prerequisite for a monolayer fixed-dose combination. Author is Brusac, Edvin; Jelicic, Mario-Livio; Amidzic Klaric, Daniela; Nigovic, Biljana; Keser, Sabina; Mornar, Ana.

Adherence in chronic diseases is a major problem which can be combated by prescribing fixed-dose combinations in the therapy of the disease. Thus, a combination of azathioprine and folic acid in the treatment of inflammatory bowel disease is highly required, but prior to formulation development, chem. compatibility of the two drugs needs to be investigated. In this work, differential scanning calorimetry, isothermal stress testing, in vitro dissolution and forced degradation studies were utilized to investigate compatibility. Moreover, a stability-indicating HPLC-DAD method for the determination of parent drugs and five of their impurities was developed, validated and applied to the inhouse sample. Compatibility testing revealed no noteworthy interactions of the two drug substances. Furthermore, forced degradation showed no substantial differences between the degradation profiles of each active pharmaceutical ingredient, their mixture and the inhouse sample, further reinforcing the claim of compatibility. Lastly, the inhouse sample was analyzed: it was shown to conform to the requirements of relevant regulatory documents for all the investigated analytes, demonstrating the method’s viability for use in formulation and process development. Our results give way to the possibility of realization of said fixed-dose combination.

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Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Imidazole series. XX. Aminonitroimidazoles and diaminoimidazoles》. Authors are Kochergin, P. M.; Verenikina, S. G.; Bushueva, K. S..The article about the compound:1-Methyl-4-nitro-1H-imidazol-5-aminecas:4531-54-8,SMILESS:NC1=C([N+]([O-])=O)N=CN1C).Computed Properties of C4H6N4O2. Through the article, more information about this compound (cas:4531-54-8) is conveyed.

cf. preceding abstract The aminonitroimidazoles I-XII were prepared by heating the corresponding nitrochloroimidazoles with a 8-15% alc. NH3 solution at 120-50° for 5-10 hrs. The products I, VII, and XII were obtained in the presence of CuSO4 catalyst (formula, R, m.p., and % yield 131-1.5°, 15-20; VII, iso-Bu, 108-10°, 15; VIII, H, 222.5-23°, 30.5; IX, Me, 198-9°, 39.5; X, Et, 160-1°, 58; XI, Pr, 130-1°, 32; XII, iso-Bu, 129-30°, 21.5. The hydrogenation of II in Ac2O in the presence of Raney Ni gave 1-ethyl-2-methyl-4,5-diaminoimidazole diacetate at 30-45° and initial H pressure of 10 atm. and tetraacetate at 50-80° and 100 atm.

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Reference:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem

Application In Synthesis of 1-Methyl-4-nitro-1H-imidazol-5-amine. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 1-Methyl-4-nitro-1H-imidazol-5-amine, is researched, Molecular C4H6N4O2, CAS is 4531-54-8, about A catalyst and additive-free three-component reaction of highly electrophilic azides with cyclic ketones and cycloaliphatic amines. Synthesis of novel N-heteroaryl amidines. Author is Efimov, Ilya; Beliaev, Nikolai; Beryozkina, Tetyana; Slepukhin, Pavel; Bakulev, Vasiliy.

Highly electrophilic 5-azido-1-methyl-4-nitro-1H-imidazole and sulfonyl azides were demonstrated to react with alicyclic amines and cyclic ketones in the absence of any catalyst or additive to afford novel N-(4-nitroimidazol-5-yl)- or N-sulfonylamidines resp. Based on single crystal X-ray anal., a revision of the previously reported data of Gao and co-workers on the direction of the reaction of sulfonyl azides with endocyclic enamines was made. The reaction of 2,6-diazidopyridine with an enamine, 4-(cyclohex-1-en-1-yl)morpholine, proceeded with cyclization of the azide moiety onto the pyridine C=N bond to form an amidine bearing the tetrazolo[1,5-a]pyridine fragment.

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Thiomorpholine – Wikipedia,
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Suwinski, Jerzy; Salwinska, Ewa; Watras, Jan; Widel, Maria published the article 《Nitroimidazoles. VI. Partition coefficients and tautomerism of simple nitroimidazoles》. Keywords: nitroimidazole derivative partition coefficient tautomerism.They researched the compound: 1-Methyl-4-nitro-1H-imidazol-5-amine( cas:4531-54-8 ).Computed Properties of C4H6N4O2. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:4531-54-8) here.

Octanol-water partition coefficients (P) were determined for 42 simple nitroimidazoles with Me, Cl, Br, MeO, NH2, and NO2 substituents. Correlation between log P and the substituent constants πX of Hansch and fX of Nys-Rekker was derived. For the N-methylated compounds, the average value of πN-CH3 was calculated to be -0.30. Significance of log P measurement in estimating the tautomeric equilibrium in 4(5)-nitroimidazoles is discussed in detail.

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Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem

SDS of cas: 4531-54-8. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 1-Methyl-4-nitro-1H-imidazol-5-amine, is researched, Molecular C4H6N4O2, CAS is 4531-54-8, about Synthesis of imidazo[4,5-b]pyrazine nucleosides. Author is Panzica, Raymond P.; Townsend, Leroy B..

5,6-Dimethyl-1-(β-D-ribofuranosyl)imidazo[4,5-b]pyrazine (I; R = β-D-ribofuranosyl) was prepared by glycosylation of the Me3Si derivative (I; R = Me3Si) (II), by fusion with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose, or by cycloaddition of 4,5-diamino-1-(β-D-ribofuranosyl)-imidazole with biacetyl.

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Reference:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem

Formula: C4H6N4O2. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 1-Methyl-4-nitro-1H-imidazol-5-amine, is researched, Molecular C4H6N4O2, CAS is 4531-54-8, about Synthesis of imidazo[4,5-b]pyrazine nucleosides. Author is Panzica, Raymond P.; Townsend, Leroy B..

5,6-Dimethyl-1-(β-D-ribofuranosyl)imidazo[4,5-b]pyrazine (I; R = β-D-ribofuranosyl) was prepared by glycosylation of the Me3Si derivative (I; R = Me3Si) (II), by fusion with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose, or by cycloaddition of 4,5-diamino-1-(β-D-ribofuranosyl)-imidazole with biacetyl.

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Reference:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem

Formula: C4H6N4O2. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 1-Methyl-4-nitro-1H-imidazol-5-amine, is researched, Molecular C4H6N4O2, CAS is 4531-54-8, about Synthesis of imidazo[4,5-b]pyrazine nucleosides.

5,6-Dimethyl-1-(β-D-ribofuranosyl)imidazo[4,5-b]pyrazine (I; R = β-D-ribofuranosyl) was prepared by glycosylation of the Me3Si derivative (I; R = Me3Si) (II), by fusion with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose, or by cycloaddition of 4,5-diamino-1-(β-D-ribofuranosyl)-imidazole with biacetyl.

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Reference:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem