Oxolan-3-amine → Rac-5-[3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-2h-pyrazole-3-carboxylic acid (tetrahydro-furan-3-yl)-amide

HRID 1695349Notes

Reaction equation

HRID 1695349 reaction equation
CO[C:3]([C:5]1[NH:6][N:7]=[C:8]([O:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][N:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[CH:9]=1)=[O:4].[NH2:25][CH:26]1[CH2:30][CH2:29][O:28][CH2:27]1>>[O:28]1[CH2:29][CH2:30][CH:26]([NH:25][C:3]([C:5]2[NH:6][N:7]=[C:8]([O:10][CH2:11][C:12]3[C:13]([C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][N:19]=4)=[N:14][O:15][C:16]=3[CH3:17])[CH:9]=2)=[O:4])[CH2:27]1

Participants

3

Reactant 2

HCID 3365553Oxolan-3-amineHCID 666438035-[3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid methyl ester

Product 1

HCID 49792920Rac-5-[3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-2h-pyrazole-3-carboxylic acid (tetrahydro-furan-3-yl)-amideYield 40%

Procedure

As described for example 17e, 5-[3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid methyl ester (100 mg, 0.3 mmol) was converted, using rac-3-aminotetrahydrofuran instead of 2,2,2-trifluoroethylamine, to the title compound (46 mg, 40%) which was obtained as a white solid. MS: m/e=388.2 [M+H]+.

Sources & evidence

ORD record
ord-13ca6116ea1a4a3da66962595c4ff717
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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