4-Aminotetrahydropyran → 6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-N-(tetrahydro-pyran-4-yl)-4-trifluoromethyl-nicotinamide

HRID 83171Notes

Reaction equation

HRID 83171 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.[NH2:28][CH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>>[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:25])[F:26])[C:18]([C:19]([NH:28][CH:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[O:20])=[CH:17][N:16]=1

Participants

3

Reactant 2

HCID 4192234-AminotetrahydropyranHCID 684447686-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-4-trifluoromethyl-nicotinic acid

Product 1

HCID 426290736-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-N-(tetrahydro-pyran-4-yl)-4-trifluoromethyl-nicotinamideYield 45%

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 4-aminotetrahydropyran instead of 2,2,2-trifluoroethylamine to the title compound (SiO2, ethyl acetate:dichloromethane=50:50 to 100:0, 109 mg, 45%) which was obtained as a white solid. MS: m/e=462.2 [M+H]+.

Sources & evidence

ORD record
ord-9aafd1a93acd403d875e925eecf492d8
Source dataset
uspto-grants-2014_09
Patent number
US08846719B2

Reaction notes

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