Triethylamine → 3-[3-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-ureido]-propionic Acid Methyl Ester

HRID 11629

Reaction equation

HRID 11629 reaction equation
[N+](C1C=CC(O[C:11](=[O:39])[NH:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[O:20][CH2:21][C:22]([N:24]2[CH2:29][CH2:28][N:27]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[CH2:26][C@H:25]2[CH3:38])=[O:23])=CC=1)([O-])=O.Cl.[CH3:41][O:42][C:43](=[O:47])[CH2:44][CH2:45][NH2:46].C(N(CC)CC)C>CO>[CH3:41][O:42][C:43](=[O:47])[CH2:44][CH2:45][NH:46][C:11]([NH:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[O:20][CH2:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[CH2:26][C@H:25]1[CH3:38])=[O:23])=[O:39]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 69655875(5-Chloro-2-(2-[4-(4-Fluoro-Benzyl)-(2R)-2-Methyl-Piperazin-1-Yl]-2-Oxo-Ethoxy}-Phenyl)-Carbamic Acid 4-Nitro-Phenyl Ester

Product 1

HCID 696553713-[3-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-ureido]-propionic Acid Methyl EsterYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-carbamic acid 4-nitro-phenyl ester (0.10 g, 0.18 mmol) in methanol was added β-alanine methyl ester hydrochloride (0.038 g, 0.27 mmol) and triethylamine (0.038 mL, 0.27 mmol). The reaction was stirred at ambient temperature overnight. The reaction was concentrated and purified via chromatography on silica gel to give the title compound (0.075 g).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified via chromatography on silica gel

Sources & evidence

ORD record
ord-7f71fd0844e740eab34efa62eff663d6
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Linked notes

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