Triethylamine → N-(Cyclopropylmethyl)-2-(3-iodo-4-methylpyridin-2-yl)hydrazinecarboxamide

Temperature

0 °C

A solution of cyclopropylmethanamine (0.33 mL, 3.7 mmol) in dichloromethane (2 mL) was added dropwise to a solution of triphosgene (0.39 g, 1.3 mmol) in dichloromethane (15 mL) kept at 0° C. under an argon atmosphere. After 5 minutes, a solution of triethylamine (1.0 mL, 7.2 mmol) in dichloromethane was added dropwise and the mixture was warmed to ambient tempertaure. After stirring two hours, the mixture was cooled to 0° C. and 2-hydrazinyl-3-iodo-4-methylpyridine (preparation 28b, 0.91 g, 3.6 mmol) in dichloromethane (8 mL) was added dropwise. The mixture was warmed to ambient temperature and stirred overnight. The solid precipitate was filtered, washed with diethyl ether and dried to yield the title compound (0.85 g, 68%) as a beige solid.

1. customkept at 0° C. under an argon atmosphere
2. temperaturethe mixture was warmed to ambient tempertaure
3. temperatureThe mixture was warmed to ambient temperature
4. stirringstirred overnight
5. filtrationThe solid precipitate was filtered
6. washwashed with diethyl ether
7. customdried

ORD record

ord-59a3c3f022fd41d7b24663f0ee41860d

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450341B2