2-Chloro-6-methylpyrimidine-4-carboxylic acid → 2-chloro-6-methyl-N-(1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)pyrimidine-4-carb oxamide

HRID 623653Notes

Reaction equation

HRID 623653 reaction equation
Cl.[F:2][C:3]([F:16])([F:15])[CH2:4][O:5][C:6]1[N:11]=[CH:10][C:9]([CH:12]([NH2:14])[CH3:13])=[CH:8][CH:7]=1.[Cl:17][C:18]1[N:23]=[C:22]([C:24](O)=[O:25])[CH:21]=[C:20]([CH3:27])[N:19]=1>>[Cl:17][C:18]1[N:23]=[C:22]([C:24]([NH:14][CH:12]([C:9]2[CH:10]=[N:11][C:6]([O:5][CH2:4][C:3]([F:2])([F:15])[F:16])=[CH:7][CH:8]=2)[CH3:13])=[O:25])[CH:21]=[C:20]([CH3:27])[N:19]=1

Participants

3

Reactant 2

HCID 105352132-Chloro-6-methylpyrimidine-4-carboxylic acidHCID 675094131-[6-(2,2,2-Trifluoroethoxy)-pyridin-3-yl]-ethylamine hydrochloride

Product 1

HCID 874270222-chloro-6-methyl-N-(1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)pyrimidine-4-carb oxamideYield 74%

Procedure

The title compound is prepared in 74% yield (480 mg, clear colorless oil) from (−)-1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethanamine hydrochloride (450 mg, 1.7 mmol, Amine-1, single enantiomer) and 2-chloro-6-methylpyrimidine-4-carboxylic acid (300 mg, 1.7 mmol) by the similar manner in Step-1 of Example 8.

Sources & evidence

ORD record
ord-efcde459cd1a484fa98311c46a3cdd61
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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