Triethylamine → HCID 86761750, compound

To a stirred solution of N-[1-(4-Iodo-phenyl)-ethyl]-O-methyl-hydroxylamine (2.1 g, 7.57 mmol), prepared as described in example P12, in dichloromethane (25 ml) was added triethyl amine (3.15 ml, 22.68 mmol) followed by a solution of 3-Difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride (1.5 g, 7.94 mmol) in dichloromethane (5 ml) slowly in ice cold condition. The reaction mixture was stirred at ambient temperature for 16 h. Reaction mixture was poured into 40 ml ice-water. Aqueous layer was extracted with dichloromethane (2×40 ml). The combined organic layer was washed with 2(N) HCl(2×20 ml) followed by saturated sodium bicarbonate (2×20 ml) and dried over sodium sulfate. Organic layer was concentrated under vacuum to give light yellow liquid. Crude was purified by chromatography to afford 2.05 g (62% of theory) of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid [1-(4-iodo-phenyl)ethyl]-methoxy-amide as white solid. Mp. 72-74° C.

1. customReaction mixture
2. extractionAqueous layer was extracted with dichloromethane (2×40 ml)
3. washThe combined organic layer was washed with 2(N) HCl(2×20 ml)
4. dry with materialdried over sodium sulfate
5. concentrationOrganic layer was concentrated under vacuum
6. customto give light yellow liquid
7. customCrude was purified by chromatography

ORD record

ord-16886de9bb0f43429893b003dd5e6600

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08357634B2