Cyclopropanecarbonyl chloride → 2-(cyclopropanecarboxamido)-5-fluoro-N-(1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)isonicotinamide

HRID 623582Notes

Reaction equation

HRID 623582 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:22]([F:25])=[CH:23][N:24]=1)[C:5]([NH:7][CH:8]([C:10]1[CH:11]=[N:12][C:13]([O:16][CH2:17][C:18]([F:21])([F:20])[F:19])=[CH:14][CH:15]=1)[CH3:9])=[O:6].[CH:26]1([C:29](Cl)=[O:30])[CH2:28][CH2:27]1>>[CH:26]1([C:29]([NH:1][C:2]2[CH:3]=[C:4]([C:22]([F:25])=[CH:23][N:24]=2)[C:5]([NH:7][CH:8]([C:10]2[CH:11]=[N:12][C:13]([O:16][CH2:17][C:18]([F:21])([F:19])[F:20])=[CH:14][CH:15]=2)[CH3:9])=[O:6])=[O:30])[CH2:28][CH2:27]1

Participants

3

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 675105252-amino-5-fluoro-N-(1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)isonicotinamide

Product 1

HCID 675089872-(cyclopropanecarboxamido)-5-fluoro-N-(1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)isonicotinamideYield 11%

Procedure

The title compound is prepared in 11% yield (4.4 mg) from 2-amino-5-fluoro-N-(1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)isonicotinamide (34 mg, 0.095 mmol, Step-1, single enantiomer) and cyclopropanecarbonyl chloride (20 mg, 0.19 mmol) by the similar manner in Step-2 of Example-8.

Sources & evidence

ORD record
ord-2a32c0fc2d1e4cba99fb159174879204
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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