Pyridine → (5-Chloro-2-(2-[4-(4-Fluoro-Benzyl)-(2R)-2-Methyl-Piperazin-1-Yl]-2-Oxo-Ethoxy}-Phenyl)-Carbamic Acid 4-Nitro-Phenyl Ester

HRID 11628

Reaction equation

HRID 11628 reaction equation
[NH2:1][C:2]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:3]=1[O:4][CH2:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[CH3:22])=[O:7].N1C=CC=CC=1.Cl[C:35]([O:37][C:38]1[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][CH:39]=1)=[O:36]>ClCCl>[N+:44]([C:41]1[CH:40]=[CH:39][C:38]([O:37][C:35](=[O:36])[NH:1][C:2]2[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:3]=2[O:4][CH2:5][C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH2:10][C@H:9]2[CH3:22])=[O:7])=[CH:43][CH:42]=1)([O-:46])=[O:45]

Participants

5

Reactant 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 206109862-(2-Amino-4-chloro-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanone

Product 1

HCID 69655875(5-Chloro-2-(2-[4-(4-Fluoro-Benzyl)-(2R)-2-Methyl-Piperazin-1-Yl]-2-Oxo-Ethoxy}-Phenyl)-Carbamic Acid 4-Nitro-Phenyl EsterYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-amino-4-chloro-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanone (0.14 g, 0.36 mmol) in dichloromethane (5 mL) was added pyridine (0.032 mL, 0.39 mmol) and 4-nitrophenyl chloroformate (0.079 g, 0.39 mmol). The reaction was stirred at ambient temperature for one hour and concentrated in vacuo to give the title compound (0.20 g).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cfd19eb5d2bc4c8bbfbf484c02e6d7bb
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Linked notes

Loading…