Cyclopropylamine → 5-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid cyclopropylamide

HRID 1962990Notes

Reaction equation

HRID 1962990 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[C:15]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[N:16][O:17][C:18]=2[CH2:19][OH:20])=[CH:8][N:7]=1)=O)C.[CH:28]1([NH2:31])[CH2:30][CH2:29]1>>[CH:28]1([NH:31][C:4]([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]3[C:15]([C:21]4[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=4)=[N:16][O:17][C:18]=3[CH2:19][OH:20])=[CH:8][N:7]=2)=[O:3])[CH2:30][CH2:29]1

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 666445155-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 498041665-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid cyclopropylamideYield 26%

Procedure

As described for example 29e, 5-[3-(4-fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl ester (75 mg, 0.2 mmol) was converted, at 85° C. overnight, using cyclopropylamine instead of isopropylamine, to the title compound (20 mg, 26%), which was obtained as a colourless gum. MS: m/e=384.2 [M+H]+.

Sources & evidence

ORD record
ord-4fe9529667954854b9b889f54a47f564
Source dataset
uspto-grants-2013_04
Patent number
US08415379B2

Reaction notes

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