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

HRID 1695451Notes

Reaction equation

HRID 1695451 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][O:14][C:15]3[CH:16]=[C:17]([C:21]([OH:23])=O)[N:18]([CH3:20])[N:19]=3)=[C:11]([CH2:24][OH:25])[O:10][N:9]=2)=[CH:4][CH:3]=1.[NH2:26][CH:27]1[CH2:31][CH2:30][O:29][CH2:28]1>>[O:29]1[CH2:30][CH2:31][CH:27]([NH:26][C:21]([C:17]2[N:18]([CH3:20])[N:19]=[C:15]([O:14][CH2:13][C:12]3[C:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)=[N:9][O:10][C:11]=3[CH2:24][OH:25])[CH:16]=2)=[O:23])[CH2:28]1

Participants

3

Reactant 2

HCID 3365553Oxolan-3-amineHCID 666437235-[3-(4-chloro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid

Product 1

HCID 49793133Rac-5-[3-(4-chloro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-2-methyl-2h-pyrazole-3-carboxylic acid (tetrahydro-furan-3-yl)-amideYield 61%

Procedure

As described for example 107, 5-[3-(4-chloro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid (100 mg, 0.28 mmol) was converted, using rac-3-aminotetrahydrofuran instead of 2-amino-2-methyl-1-propanol, to the title compound (73 mg, 61%) which was obtained as a colorless gum. MS: m/e=433.3 [M+H]+.

Sources & evidence

ORD record
ord-47b61aa0afa2416cab2239a3511e925f
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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