3-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzoic Acid → 2-{1-[3-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzoyl]piperidin-4-yl}-5-(3,4-dimethoxyphenyl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

HRID 524180Notes

Reaction equation

HRID 524180 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:12]2[C:13]([CH3:25])([CH3:24])[C:14](=[O:23])[N:15]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[N:16]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11].[CH:26]1([CH2:29][O:30][C:31]2[CH:32]=[C:33]([CH:37]=[CH:38][C:39]=2[O:40][CH:41]([F:43])[F:42])[C:34](O)=[O:35])[CH2:28][CH2:27]1>>[CH:26]1([CH2:29][O:30][C:31]2[CH:32]=[C:33]([CH:37]=[CH:38][C:39]=2[O:40][CH:41]([F:42])[F:43])[C:34]([N:20]2[CH2:21][CH2:22][CH:17]([N:15]3[C:14](=[O:23])[C:13]([CH3:25])([CH3:24])[C:12]([C:6]4[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:4]([O:3][CH3:2])[CH:5]=4)=[N:16]3)[CH2:18][CH2:19]2)=[O:35])[CH2:28][CH2:27]1

Participants

3

Reactant 2

HCID 23940063-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzoic AcidHCID 666164065-(3,4-dimethoxyphenyl)-4,4-dimethyl-2-piperidin-4-yl-2,4-dihydro-3H-pyrazol-3-one hydrochloride2×

Product 1

HCID 462049622-{1-[3-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzoyl]piperidin-4-yl}-5-(3,4-dimethoxyphenyl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

Procedure

The title compound is prepared analogously as described for GP2-WU2 using 5-(3,4-dimethoxyphenyl)-4,4-dimethyl-2-(piperidin-4-yl)-2,4-dihydro-3H-pyrazol-3-one (compound B1) and 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoic acid as starting compounds. The crude product is purified by chromatography (amino phase silica gel and DCM) to yield the title compound.

Workup

  1. customThe title compound is prepared analogously
  2. customThe crude product is purified by chromatography (amino phase silica gel and DCM)

Sources & evidence

ORD record
ord-548ba1cfc2464c05b9dbb4f1cc1f3524
Source dataset
uspto-grants-2016_05
Patent number
US09340522B2

Reaction notes

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