Cyclopropanemethanamine → 5-[3-(4-Fluoro-phenyl)-isoxazol-4-ylmethoxy]-pyrazine-2-carboxylic acid cyclopropylmethyl-amide

HRID 600494Notes

Reaction equation

HRID 600494 reaction equation
CO[C:3]([C:5]1[CH:10]=[N:9][C:8]([O:11][CH2:12][C:13]2[C:14]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[N:15][O:16][CH:17]=2)=[CH:7][N:6]=1)=[O:4].[NH2:25][CH2:26][CH:27]1[CH2:29][CH2:28]1>>[CH:27]1([CH2:26][NH:25][C:3]([C:5]2[CH:10]=[N:9][C:8]([O:11][CH2:12][C:13]3[C:14]([C:18]4[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=4)=[N:15][O:16][CH:17]=3)=[CH:7][N:6]=2)=[O:4])[CH2:29][CH2:28]1

Participants

3

Reactant 2

HCID 75646CyclopropanemethanamineHCID 684464005-[3-(4-Fluoro-phenyl)-isoxazol-4-ylmethoxy]-pyrazine-2-carboxylic acid methyl ester

Product 1

HCID 469379005-[3-(4-Fluoro-phenyl)-isoxazol-4-ylmethoxy]-pyrazine-2-carboxylic acid cyclopropylmethyl-amideYield 52%

Procedure

As described for example 13 g, 5-[3-(4-fluoro-phenyl)-isoxazol-4-ylmethoxy]-pyrazine-2-carboxylic acid methyl ester (75 mg, 0.23 mmol) was converted, using aminomethylcyclopropane instead of 2,2,2-trifluoroethylamine, to the title compound (44 mg, 52%) which was obtained as a light yellow solid. MS: m/e=427.0 [M+OAc]+.

Sources & evidence

ORD record
ord-3b18a66f78854115a5d6b6fa705f1851
Source dataset
uspto-grants-2011_03
Patent number
US07902201B2

Reaction notes

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