4,4-Difluoropiperidine hydrochloride → {5-[3-(4-Chloro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazol-3-yl}-(4,4-difluoro-piperidin-1-yl)-methanone

HRID 1695452Notes

Reaction equation

HRID 1695452 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](O)=[O:22])[N:18]([CH3:20])[N:19]=3)=[C:11]([CH2:24][OH:25])[O:10][N:9]=2)=[CH:4][CH:3]=1.Cl.[F:27][C:28]1([F:34])[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH2:13][O:14][C:15]3[CH:16]=[C:17]([C:21]([N:31]4[CH2:32][CH2:33][C:28]([F:34])([F:27])[CH2:29][CH2:30]4)=[O:22])[N:18]([CH3:20])[N:19]=3)=[C:11]([CH2:24][OH:25])[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 27583514,4-Difluoropiperidine hydrochlorideHCID 666437235-[3-(4-chloro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid

Product 1

HCID 49793016{5-[3-(4-Chloro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazol-3-yl}-(4,4-difluoro-piperidin-1-yl)-methanoneYield 67%

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 4,4-difluoropiperidine hydrochloride instead of 2-amino-2-methyl-1-propanol, to the title compound (87 mg, 67%) which was obtained as a colorless gum. MS: m/e=467.2 [M+H]+.

Sources & evidence

ORD record
ord-3b320a1a2c3e401c8e0f911cdfbf184c
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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