Oxolan-3-amine → Rac-5-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-2h-pyrazole-3-carboxylic acid (tetrahydrofuran-3-yl)-amide

HRID 1695364Notes

Reaction equation

HRID 1695364 reaction equation
CO[C:3]([C:5]1[NH:6][N:7]=[C:8]([O:10][CH2:11][C:12]2[C:13]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:14][O:15][C:16]=2[CH3:17])[CH:9]=1)=[O:4].[NH2:22][CH:23]1[CH2:27][CH2:26][O:25][CH2:24]1>>[O:25]1[CH2:26][CH2:27][CH:23]([NH:22][C:3]([C:5]2[NH:6][N:7]=[C:8]([O:10][CH2:11][C:12]3[C:13]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:14][O:15][C:16]=3[CH3:17])[CH:9]=2)=[O:4])[CH2:24]1

Participants

3

Reactant 2

HCID 3365553Oxolan-3-amineHCID 66643879HCID 66643879, compound

Product 1

HCID 59568399Rac-5-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-2h-pyrazole-3-carboxylic acid (tetrahydrofuran-3-yl)-amideYield 48%

Procedure

As described for example 26d, 5-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid methyl ester (492 mg, 1.7 mmol) was converted, using rac-3-aminotetrahydrofuran instead of 4-aminotetrahydropyran, to the title compound (280 mg, 48%) which was obtained as a colorless oil. MS: m/e=349.2 [M+H]+.

Sources & evidence

ORD record
ord-7dbac6df87774d9897911387db49d93a
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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