5-(Benzyloxy)-2-methylbenzoic acid → 5-[3-(Benzyloxy)-4-methoxyphenyl]-2-(1-{[5-(benzyloxy)-2-methylphenyl]carbonyl}piperidin-4-yl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

HRID 1914218Notes

Reaction equation

HRID 1914218 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([C:18]2[C:19]([CH3:31])([CH3:30])[C:20](=[O:29])[N:21]([CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[N:22]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:32]([O:39][C:40]1[CH:41]=[CH:42][C:43]([CH3:49])=[C:44]([CH:48]=1)[C:45](O)=[O:46])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([C:18]2[C:19]([CH3:31])([CH3:30])[C:20](=[O:29])[N:21]([CH:23]3[CH2:24][CH2:25][N:26]([C:45]([C:44]4[CH:48]=[C:40]([O:39][CH2:32][C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)[CH:41]=[CH:42][C:43]=4[CH3:49])=[O:46])[CH2:27][CH2:28]3)[N:22]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 597600475-(Benzyloxy)-2-methylbenzoic acid2×HCID 666165115-[3-(benzyloxy)-4-methoxyphenyl]-4,4-dimethyl-2-piperidin-4-yl-2,4-dihydro-3H-pyrazol-3-one hydrochloride2×

Product 1

HCID 673663165-[3-(Benzyloxy)-4-methoxyphenyl]-2-(1-{[5-(benzyloxy)-2-methylphenyl]carbonyl}piperidin-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-[3-(benzyloxy)-4-methoxyphenyl]-4,4-dimethyl-2-(piperidin-4-yl)-2,4-dihydro-3H-pyrazol-3-one hydrochloride (compound B4*HCl) and 5-(benzyloxy)-2-methylbenzoic acid (compound F1) 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-8ab1ea772d5a43df8aca20a15d72bf8f
Source dataset
uspto-grants-2013_12
Patent number
US08609848B2

Reaction notes

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