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

HRID 1695381Notes

Reaction equation

HRID 1695381 reaction equation
CO[C:3]([C:5]1[N:6]([CH3:24])[N:7]=[C:8]([O:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[CH:9]=1)=[O:4].COC(C1NN=C([O:34][CH2:35][C:36]2[C:37]([C:42]3C=CC=CC=3)=[N:38]OC=2C)C=1)=O.NC1CCOC1>>[O:34]1[CH2:35][CH2:36][CH:37]([NH:38][C:3]([C:5]2[N:6]([CH3:24])[N:7]=[C:8]([O:10][CH2:11][C:12]3[C:13]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)=[N:14][O:15][C:16]=3[CH3:17])[CH:9]=2)=[O:4])[CH2:42]1

Participants

4

Reactant 3

HCID 3365553Oxolan-3-amineHCID 666438022-Methyl-5-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid methyl esterHCID 66643884HCID 66643884, compound

Product 1

HCID 49792992Rac-2-methyl-5-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-2h-pyrazole-3-carboxylic acid (tetrahydro-furan-3-yl)-amideYield 80%

Procedure

As described for example 1b, 2-methyl-5-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid methyl ester (30 mg, 0.09 mmol), instead of 5-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid methyl ester, was converted, using rac-3-aminotetrahydrofuran instead of morpholine, to the title compound (28 mg, 80%) which was obtained as a colorless oil. MS: m/e=383.2 [M+H]+.

Sources & evidence

ORD record
ord-2baf82d3fe404d13a966706c0bc1cacd
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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