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

HRID 1695414Notes

Reaction equation

HRID 1695414 reaction equation
CO[C:3]([C:5]1[N:6]([CH3:25])[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].COC(C1NN=C([O:35][CH2:36][C:37]2[C:38]([C:43]3C=CC=CC=3)=[N:39]OC=2C)C=1)=O.NC1CCOC1>>[O:35]1[CH2:36][CH2:37][CH:38]([NH:39][C:3]([C:5]2[N:6]([CH3:25])[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])[CH2:43]1

Participants

4

Reactant 3

HCID 3365553Oxolan-3-amineHCID 666436965-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid methyl esterHCID 66643884HCID 66643884, compound

Product 1

HCID 59568407Rac-5-[3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-car-boxylic acid (tetrahydro-furan-3-yl)-amideYield 59%

Procedure

As described for example 1b, 5-[3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (140 mg, 0.40 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 (96 mg, 59%) which was obtained as a white solid. MS: m/e=402.3 [M+H]+.

Sources & evidence

ORD record
ord-50449aae0486451ba42f9e1bc48eb68f
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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