4,4-Difluoropiperidine hydrochloride → (4,4-Difluoro-piperidin-1-yl)-[6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridin-3-yl]-methanone

HRID 83159Notes

Reaction equation

HRID 83159 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=1.Cl.[F:25][C:26]1([F:32])[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>>[F:25][C:26]1([F:32])[CH2:31][CH2:30][N:29]([C:19]([C:18]2[CH:17]=[N:16][C:15]([O:14][CH2:13][C:3]3[C:4]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)=[N:5][O:6][C:2]=3[CH3:1])=[CH:23][CH:22]=2)=[O:21])[CH2:28][CH2:27]1

Participants

3

Reactant 2

HCID 27583514,4-Difluoropiperidine hydrochlorideHCID 665992136-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid

Product 1

HCID 68936616(4,4-Difluoro-piperidin-1-yl)-[6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridin-3-yl]-methanoneYield 98%

Procedure

As described for example 8b, 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid (100 mg, 0.32 mmol) was converted, using 4,4-difluoropiperidine hydrochloride (1 M in DMF) instead of methylamine, to the title compound (131 mg, 98%) which was obtained as a light yellow gum. MS: m/e=414.4 [M+H]+.

Sources & evidence

ORD record
ord-c235b749b3fb4793959afaef71f0ab31
Source dataset
uspto-grants-2014_09
Patent number
US08846719B2

Reaction notes

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