2,5-Dimethylbenzoic acid → 2-{1-[(2,5-Dimethylphenyl)carbonyl]piperidin-4-yl}-5-(7-methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-4-yl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

HRID 524265

Reaction equation

HRID 524265 reaction equation
Cl.[CH3:2][O:3][C:4]1[C:12]2[O:11][C:10]([CH3:14])([CH3:13])[CH2:9][C:8]=2[C:7]([C:15]2[C:16]([CH3:28])([CH3:27])[C:17](=[O:26])[N:18]([CH:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[N:19]=2)=[CH:6][CH:5]=1.[CH3:29][C:30]1[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][C:31]=1[C:32](O)=[O:33]>>[CH3:29][C:30]1[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][C:31]=1[C:32]([N:23]1[CH2:24][CH2:25][CH:20]([N:18]2[C:17](=[O:26])[C:16]([CH3:28])([CH3:27])[C:15]([C:7]3[C:8]4[CH2:9][C:10]([CH3:14])([CH3:13])[O:11][C:12]=4[C:4]([O:3][CH3:2])=[CH:5][CH:6]=3)=[N:19]2)[CH2:21][CH2:22]1)=[O:33]

Participants

3

Reactant 2

HCID 118922,5-Dimethylbenzoic acidHCID 666165905-(7-methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-4-yl)-4,4-dimethyl-2-(piperidin-4-yl)-2,4-dihydro-3H-pyrazol-3-one hydrochloride2×

Product 1

HCID 673645012-{1-[(2,5-Dimethylphenyl)carbonyl]piperidin-4-yl}-5-(7-methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-4-yl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

Procedure

The title compound is prepared analogously as described for GP2-WU2 using 5-(7-methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-4-yl)-4,4-dimethyl-2-piperidin-4-yl-2,4-dihydro-3H-pyrazol-3-one (compound B5) and 2,5-dimethylbenzoic acid as starting compounds. The crude product is purified by chromatography (amino phase silica gel and DCM) and by crystallization from DCM and diethyl ether 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) and by crystallization from DCM and diethyl ether

Sources & evidence

ORD record
ord-c722d8f1d5b6478f956a441811d06f4b
Source dataset
uspto-grants-2016_05
Patent number
US09340522B2

Linked notes

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