4-(Dimethylamino)-1-naphthoic acid → 5-(3,4-Dimethoxyphenyl)-2-(1-{[4-(dimethylamino)naphthalen-1-yl]carbonyl}piperidin-4-yl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

HRID 1914188Notes

Reaction equation

HRID 1914188 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].[CH3:26][N:27]([CH3:41])[C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([C:38](O)=[O:39])=[CH:30][CH:29]=1>>[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][N:20]([C:38]([C:31]4[C:32]5[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=5)[C:28]([N:27]([CH3:41])[CH3:26])=[CH:29][CH:30]=4)=[O:39])[CH2:19][CH2:18]3)[N:16]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

3

Reactant 2

HCID 5226954-(Dimethylamino)-1-naphthoic acidHCID 666164065-(3,4-dimethoxyphenyl)-4,4-dimethyl-2-piperidin-4-yl-2,4-dihydro-3H-pyrazol-3-one hydrochloride2×

Product 1

HCID 673634585-(3,4-Dimethoxyphenyl)-2-(1-{[4-(dimethylamino)naphthalen-1-yl]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-WU1 using 5-(3,4-dimethoxyphenyl)-4,4-dimethyl-2-(piperidin-4-yl)-2,4-dihydro-3H-pyrazol-3-one (compound B1) and 4-(dimethylamino)naphthalene-1-carboxylic acid as starting compounds. The crude product is purified by crystallization from diethyl ether to yield the title compound.

Workup

  1. customThe title compound is prepared analogously
  2. customThe crude product is purified by crystallization from diethyl ether

Sources & evidence

ORD record
ord-99b70ca99e4f4a22aeb7ae836b92b429
Source dataset
uspto-grants-2013_12
Patent number
US08609848B2

Reaction notes

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