2-Aminopropanol → Rac-5-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-2-methyl-2h-pyrazole-3-carboxylic acid (2-hydroxy-1-methyl-ethyl)-amide

HRID 1695418Notes

Reaction equation

CO[C:3]([C:5]1[N:6]([CH3:22])[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].[CH3:23][CH:24]([NH2:27])[CH2:25][OH:26]>>[OH:26][CH2:25][CH:24]([NH:27][C:3]([C:5]1[N:6]([CH3:22])[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])[CH3:23]

Participants

Reactant 2

HCID 51262-Aminopropanol

HCID 66643838HCID 66643838, compound

Product 1

HCID 59568446Rac-5-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-2-methyl-2h-pyrazole-3-carboxylic acid (2-hydroxy-1-methyl-ethyl)-amideYield 70%

Procedure

As described for example 85b, 5-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (60 mg, 0.2 mmol), was converted, using DL-2-amino-1-propanol instead of ethanolamine, to the title compound (48 mg, 70%) which was obtained as a colorless oil. MS: m/e=351.3 [M+H]+.

Sources & evidence

ORD record: ord-61b93972b2614cc8b664d32bfbbd779c
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163728B2

Reaction notes

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