Cyclopropanemethanamine → 2-{(E)-2-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-vinyl}-4-methyl-thiazole-5-carboxylic acid cyclopropylmethyl-amide

HRID 1923579Notes

Reaction equation

HRID 1923579 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12](/[CH:13]=[CH:14]/[C:15]3[S:16][C:17]([C:21]([OH:23])=O)=[C:18]([CH3:20])[N:19]=3)=[C:11]([CH3:24])[O:10][N:9]=2)=[N:6][CH:7]=1.[NH2:25][CH2:26][CH:27]1[CH2:29][CH2:28]1>>[CH:27]1([CH2:26][NH:25][C:21]([C:17]2[S:16][C:15](/[CH:14]=[CH:13]/[C:12]3[C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=4)=[N:9][O:10][C:11]=3[CH3:24])=[N:19][C:18]=2[CH3:20])=[O:23])[CH2:29][CH2:28]1

Participants

3

Reactant 2

HCID 75646CyclopropanemethanamineHCID 666436302-{(E)-2-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-vinyl}-4-methyl-thiazole-5-carboxylic acid

Product 1

HCID 595684902-{(E)-2-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-vinyl}-4-methyl-thiazole-5-carboxylic acid cyclopropylmethyl-amideYield 67%

Procedure

As described for example 71d, 2-{(E)-2-[3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-vinyl}-4-methyl-thiazole-5-carboxylic acid (69 mg, 0.2 mmol) was converted, using aminomethylcyclopropane instead of isopropylamine, to the title compound (53 mg, 67%) which was obtained as a white solid. MS: m/e=399.1 [M+H]+.

Sources & evidence

ORD record
ord-fb86047d8dbd4530a71eeed67b6f6a51
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

Loading…