1,1,1-Trifluoro-2-propanamine → 6-[3-(4-Chloro-phenyl)-isoxazol-4-ylmethoxy]-n-((s)-2,2,2-trifluoro-1-methyl-ethyl)-nicotinamide

HRID 1897353Notes

Reaction equation

HRID 1897353 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][O:14][C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=3)=[CH:11][O:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:24][CH:25]([NH2:30])[C:26]([F:29])([F:28])[F:27]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH2:13][O:14][C:15]3[CH:23]=[CH:22][C:18]([C:19]([NH:30][C@@H:25]([CH3:24])[C:26]([F:29])([F:28])[F:27])=[O:21])=[CH:17][N:16]=3)=[CH:11][O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 37831651,1,1-Trifluoro-2-propanamineHCID 684437696-[3-(4-Chloro-phenyl)-isoxazol-4-ylmethoxy]-nicotinic acid

Product 1

HCID 684454956-[3-(4-Chloro-phenyl)-isoxazol-4-ylmethoxy]-n-((s)-2,2,2-trifluoro-1-methyl-ethyl)-nicotinamideYield 98%

Procedure

As described for example 346b, 6-[3-(4-chloro-phenyl)-isoxazol-4-ylmethoxy]-nicotinic acid (150 mg, 0.45 mmol) was converted, using L-2,2,2-trifluoro-1-(methyl)ethylamine instead of ethanolamine, to the title compound (190 mg, 98%) which was obtained as a white solid. MS: m/e=424.0 [M−H]−.

Sources & evidence

ORD record
ord-afe9d569ada64fccad9abfbb02c4c94b
Source dataset
uspto-grants-2013_08
Patent number
US08518974B2

Reaction notes

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