1,1,1-Trifluoro-2-propanamine → 6-((3-Butyl-5-methyl-isoxazol-4-yl)methoxy)-n-((s)-2,2,2-trifluoro-1-methyl-ethyl)-nicotinamide

HRID 1807506Notes

Reaction equation

HRID 1807506 reaction equation
[CH2:1]([C:5]1[C:9]([CH2:10][O:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][N:13]=2)=[C:8]([CH3:21])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4].[CH3:22][CH:23]([NH2:28])[C:24]([F:27])([F:26])[F:25]>>[CH2:1]([C:5]1[C:9]([CH2:10][O:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([NH:28][C@@H:23]([CH3:22])[C:24]([F:27])([F:26])[F:25])=[O:18])=[CH:14][N:13]=2)=[C:8]([CH3:21])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 37831651,1,1-Trifluoro-2-propanamineHCID 665983356-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid

Product 1

HCID 498007346-((3-Butyl-5-methyl-isoxazol-4-yl)methoxy)-n-((s)-2,2,2-trifluoro-1-methyl-ethyl)-nicotinamideYield 61%

Procedure

As described for example 19b, 6-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid (100 mg, 0.34 mmol) was converted, using L-2,2,2-trifluoro-1-(methyl)ethylamine (ABCR AB146651) instead of L-2,2,2-trifluoro-1-(methyl)ethylamine (ABCR F07820EFA), to the title compound (81 mg, 61%) which was obtained as a light yellow oil after purification by chromatography (silica, heptane:ethyl acetate=1:0 to 2:1). MS: m/e=384.3 [M−H]−.

Sources & evidence

ORD record
ord-5f2ed160e46147a3a99e07a18bf6b810
Source dataset
uspto-grants-2013_01
Patent number
US08357703B2

Reaction notes

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