Isopropylamine → N-Isopropyl-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-4-trifluoromethyl-nicotinamide

HRID 331769Notes

Reaction equation

HRID 331769 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][O:14][C:15]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[C:18]([C:19](O)=[O:20])=[CH:17][N:16]=1.[CH:28]([NH2:31])([CH3:30])[CH3:29]>>[CH:28]([NH:31][C:19](=[O:20])[C:18]1[C:22]([C:24]([F:27])([F:25])[F:26])=[CH:23][C:15]([O:14][CH2:13][C:3]2[C:4]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[N:5][O:6][C:2]=2[CH3:1])=[N:16][CH:17]=1)([CH3:30])[CH3:29]

Participants

3

Reactant 2

HCID 6363IsopropylamineHCID 684447686-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-4-trifluoromethyl-nicotinic acid

Product 1

HCID 68444535N-Isopropyl-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-4-trifluoromethyl-nicotinamideYield 27%

Procedure

As described for example 12, 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-4-trifluoromethyl-nicotinic acid (200 mg, 0.53 mmol) instead of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid was converted using isopropylamine instead of 2,2,2-trifluoroethylamine to the title compound (SiO2, ethyl acetate:dichloromethane=100:0 to 50:50, 60 mg, 27%) which was obtained as an off white solid. MS: m/e=420.1 [M+H]+.

Sources & evidence

ORD record
ord-562752cb823a4ea1bd6f906722b25585
Source dataset
uspto-grants-2014_11
Patent number
US08877782B2

Reaction notes

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