Methyl bromoacetate → [4-(3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-piperazin-1-yl]-acetic Acid Methyl Ester

HRID 902702Notes

Reaction equation

HRID 902702 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)[CH:12]=1.[CH3:45][O:46][C:47](=[O:50])[CH2:48]Br.C(N(C(C)C)CC)(C)C>CO>[CH3:45][O:46][C:47](=[O:50])[CH2:48][N:20]1[CH2:19][CH2:18][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:44])[F:43])[C:3]=3[Cl:2])[CH2:23][CH:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:12]=2)[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 60984Methyl bromoacetateHCID 81531DiisopropylethylamineHCID 69253147HCID 69253147, compound

Product 1

HCID 69252741[4-(3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-piperazin-1-yl]-acetic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (2-chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-[3-(3-piperazin-1-yl-phenoxy)-propyl]-amine hydrochloride (114 mg, 0.187 mmol—Example 168) in methanol (15 mL) was treated with bromo-acetic acid methyl ester (57 mg, 0.375 mmol) and diisopropyl-ethyl-amine (48 mg, 0.375 mmol). The resulting solution was heated at 50° C. for 3 hours, cooled to room temperature, and concentrated. The crude material was dissolved in EtOAc and washed with water (1×). The organic layer was then washed with brine (1×), dried over sodium sulfate, and filtered. The EtOAc was concentrated and the sample was dried under vacuum to title compound as an oil (99 mg, 78%). MS(ES) m/e 622.2 ([M−COOCH3]+).

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. dissolutionThe crude material was dissolved in EtOAc
  4. washwashed with water (1×)
  5. washThe organic layer was then washed with brine (1×)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationThe EtOAc was concentrated
  9. dry with materialthe sample was dried under vacuum to title compound as an oil (99 mg, 78%)

Sources & evidence

ORD record
ord-b800edf30ce648d49d87c87374d9d9c6
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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