Ethanamine, 2,2,2-trifluoro- → 6-(5-Methyl-3-pyridin-4-yl-isoxazol-4-ylmethoxy)-N-(2,2,2-trifluoro-ethyl)-nicotinamide

HRID 83272Notes

Reaction equation

HRID 83272 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=1.COC(=O)C1C=CC(OCC2C(C3C=CC=C(F)C=3)=NOC=2C)=NC=1.[F:49][C:50]([F:54])([F:53])[CH2:51][NH2:52]>>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:8]=[CH:9][N:10]=[CH:11][CH:12]=2)[C:3]=1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH:52][CH2:51][C:50]([F:54])([F:53])[F:49])=[O:21])=[CH:17][N:16]=1

Participants

4

Reactant 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 684418946-[3-(3-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl esterHCID 684422916-(5-Methyl-3-pyridin-4-yl-isoxazol-4-ylmethoxy)-nicotinic acid

Product 1

HCID 426293346-(5-Methyl-3-pyridin-4-yl-isoxazol-4-ylmethoxy)-N-(2,2,2-trifluoro-ethyl)-nicotinamideYield 14%

Procedure

As described for example 92, 6-(5-methyl-3-pyridin-4-yl-isoxazol-4-ylmethoxy)-nicotinic acid (93 mg, 0.3 mmol), instead of 6-[3-(3-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (103 mg, 0.3 mmol) was converted, using 2,2,2-trifluoroethylamine instead of cyclopropylamine, to the title compound (16 mg, 14%) which was obtained as a light brown solid. MS: m/e=393.3 [M+H]+.

Sources & evidence

ORD record
ord-4c0342bfe1b24857b776058c2f5969d0
Source dataset
uspto-grants-2014_09
Patent number
US08846719B2

Reaction notes

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