Ethanamine, 2,2,2-trifluoro- → 2-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-N-(2,2,2-trifluoro-ethyl)-isonicotinamide

HRID 1897063Notes

Reaction equation

HRID 1897063 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:16]=[C:17]([CH:21]=[CH:22][N:23]=1)[C:18]([OH:20])=O.CC1ON=C(C2C=CC=CC=2)C=1COC1C=CC(C(O)=O)=CN=1.[F:47][C:48]([F:52])([F:51])[CH2:49][NH2:50]>>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][N:23]=1)[C:18]([NH:50][CH2:49][C:48]([F:52])([F:51])[F:47])=[O:20]

Participants

4

Reactant 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 665992136-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acidHCID 684441282-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isonicotinic acid

Product 1

HCID 426290722-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-N-(2,2,2-trifluoro-ethyl)-isonicotinamideYield 51%

Procedure

As described for example 8b, 2-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-isonicotinic acid (78 mg, 0.3 mmol), instead of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid, was converted, using 2,2,2-trifluoroethylamine instead of methylamine, to the title compound (49 mg, 51%) which was obtained as a white solid. MS: m/e=392.3 [M+H]+.

Sources & evidence

ORD record
ord-81bcf2220a6741a6a7c692e28875529e
Source dataset
uspto-grants-2013_08
Patent number
US08518974B2

Reaction notes

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