Methyl bromoacetate → [4-(6-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-amino]-propoxy}-pyridin-2-yl)-piperazin-1-yl]-acetic Acid Methyl Ester

HRID 902655Notes

Reaction equation

HRID 902655 reaction equation
Cl.[Cl:2][C:3]1[C:40]([C:41]([F:44])([F:43])[F:42])=[CH:39][CH:38]=[CH:37][C:4]=1[CH2:5][N:6]([CH2:23][CH:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[N:12]=1.Br[CH2:46][C:47]([O:49][CH3:50])=[O:48].C(N(C(C)C)CC)(C)C>CCO>[CH3:50][O:49][C:47](=[O:48])[CH2:46][N:20]1[CH2:21][CH2:22][N:17]([C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([O:10][CH2:9][CH2:8][CH2:7][N:6]([CH2:5][C:4]3[CH:37]=[CH:38][CH:39]=[C:40]([C:41]([F:42])([F:43])[F:44])[C:3]=3[Cl:2])[CH2:23][CH:24]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:12]=2)[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 60984Methyl bromoacetateHCID 81531DiisopropylethylamineHCID 69253044(2-Chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-[3-(6-piperazin-1-yl-pyridin-2-yloxy)-propyl]-amine Hydrochloride

Product 1

HCID 69253888[4-(6-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-amino]-propoxy}-pyridin-2-yl)-piperazin-1-yl]-acetic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring solution of (2-Chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-[3-(6-piperazin-1-yl-pyridin-2-yloxy)-propyl]-amine hydrochloride (0.1 g, 0.16 mmol) in EtOH (6 ml) was added methyl bromo-acetate (16 uL, 0.17 mmol) and diisopropylethylamine (89 uL, 0.51 mmol). The reaction mixture was stirred for 10 h at RT and then concentrated. Purification by flash silica gel chromatograpy afforded the title compound as a clear oil, 47 mg (42%). MS (ESI) 681.2 (M+).

Workup

  1. concentrationconcentrated
  2. customPurification by flash silica gel chromatograpy

Sources & evidence

ORD record
ord-c92b19e141c8435b951af23ef401d84c
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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