4-Aminotetrahydropyran → 5-{[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-amino}-2H-pyrazole-3-carboxylic acid (tetrahydro-pyran-4-yl)-amide

HRID 1695500Notes

Reaction equation

HRID 1695500 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][NH:14][C:15]3[CH:16]=[C:17]([C:20]([OH:22])=O)[NH:18][N:19]=3)=[C:11]([CH3:23])[O:10][N:9]=2)=[CH:4][CH:3]=1.[NH2:24][CH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>>[O:28]1[CH2:29][CH2:30][CH:25]([NH:24][C:20]([C:17]2[NH:18][N:19]=[C:15]([NH:14][CH2:13][C:12]3[C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)=[N:9][O:10][C:11]=3[CH3:23])[CH:16]=2)=[O:22])[CH2:26][CH2:27]1

Participants

3

Reactant 2

HCID 4192234-AminotetrahydropyranHCID 666437645-{[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-amino}-2H-pyrazole-3-carboxylic acid

Product 1

HCID 497931315-{[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-amino}-2H-pyrazole-3-carboxylic acid (tetrahydro-pyran-4-yl)-amideYield 28%

Procedure

As described for example 152, 5-{[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-amino}-2H-pyrazole-3-carboxylic acid was converted, using 4-aminotetrahydropyran instead of 2-hydroxy-2-methylpropylamine, to the title compound (9.1 mg, 28%) which was obtained as an off white solid. MS: m/e=400.2 [M+H]+.

Sources & evidence

ORD record
ord-11c2c15405e04e7ba9087f14db625df1
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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