As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 76176-87-9, name is Thiomorpholine-1-oxide hydrochloride. This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 76176-87-9
A solution of lambda/-(7-chloro-2-methylpyrazolo[l,5-alpha]pyrimidin-5-yl)-4-(2- hydroxypropan-2-yl)benzamide (2F, 52 mg, 0.151 mmol), thiomorpholine-iS’-oxide hydrochloride (91 mg, 0.557 mmol), and JV,jV-diisopropylethylamine (79 mg, 0.467 mmol) in DMF (1.11 mL) was stirred at 100 0C for 3.5h. After cooling to room temperature, the mixture was diluted with methanol, and was then purified by preparatory HPLC (25-30% MeCNZH2O gradient + 0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white solid (29.3 mg, 24%). 1H NMR (400 MHz, DMSO-J6) delta ppm 1.45 (s, 6 H), 2.39 (s, 3 H), 2.93 (dd, J=12.13, 1.77 Hz, 2 H), 3.09 – 3.22 (m, 2 H), 3.99 – 4.09 (m, 2 H), 4.40 (d, J=14.40 Hz, 2 H), 6.19 (s, 1 H), 7.43 (s, 1 H), 7.60 (d, J=8.59 Hz, 2 H), 8.00 (d, J=8.59 Hz, 2 H), 10.89 (s, 1 H); ESI-MS: m/z 428.3 (M+H)+.
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Reference£º
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2009/123986; (2009); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem