Cyclopropanemethanamine → N-Cyclopropylmethyl-6-[3-(4-fluoro-phenyl)-5-trifluoromethyl-isoxazol-4-ylmethoxy]-nicotinamide

HRID 83266Notes

Reaction equation

HRID 83266 reaction equation
CO[C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[N:14][O:15][C:16]=2[C:17]([F:20])([F:19])[F:18])=[N:6][CH:5]=1.[CH:29]1([CH2:32][NH2:33])[CH2:31][CH2:30]1>>[CH:29]1([CH2:32][NH:33][C:3](=[O:28])[C:4]2[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]3[C:13]([C:21]4[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=4)=[N:14][O:15][C:16]=3[C:17]([F:20])([F:19])[F:18])=[N:6][CH:5]=2)[CH2:31][CH2:30]1

Participants

3

Reactant 2

HCID 75646CyclopropanemethanamineHCID 684447756-[3-(4-Fluoro-phenyl)-5-trifluoromethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester

Product 1

HCID 68932423N-Cyclopropylmethyl-6-[3-(4-fluoro-phenyl)-5-trifluoromethyl-isoxazol-4-ylmethoxy]-nicotinamideYield 87%

Procedure

As described for example 137, 6-[3-(4-fluoro-phenyl)-5-trifluoromethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (100 mg, 0.25 mmol) was converted, using cyclopropanemethylamine instead of methylamine, to the title compound (96 mg, 87%) which was obtained as an off white solid. MS: m/e=436.0 [M+H]+.

Sources & evidence

ORD record
ord-67965a52be874d07a29bbe4430b8a694
Source dataset
uspto-grants-2014_09
Patent number
US08846719B2

Reaction notes

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