2-Propenoic acid, 3-(4-chlorophenyl)- → (2E)-3-(4-Chlorophenyl)-N-[(1S)-2-[[2-[4-(4-chlorophenyl)-1-piperazinyl]-2-oxoethyl]amino]-2-oxo-1-(2-pyridylmethyl)ethyl]-2-propenamide

HRID 2416644Notes

Reaction equation

HRID 2416644 reaction equation
[NH2:1][C@@H:2]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)[C:3]([NH:5][CH2:6][C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)=[O:8])=[O:4].[Cl:29][C:30]1[CH:40]=[CH:39][C:33]([CH:34]=[CH:35][C:36](O)=[O:37])=[CH:32][CH:31]=1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[Cl:29][C:30]1[CH:31]=[CH:32][C:33](/[CH:34]=[CH:35]/[C:36]([NH:1][C@@H:2]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[C:3]([NH:5][CH2:6][C:7]([N:9]2[CH2:10][CH2:11][N:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[CH2:13][CH2:14]2)=[O:8])=[O:4])=[O:37])=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 153712-Propenoic acid, 3-(4-chlorophenyl)-HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69933682HCID 69933682, compound

Product 1

HCID 69935218(2E)-3-(4-Chlorophenyl)-N-[(1S)-2-[[2-[4-(4-chlorophenyl)-1-piperazinyl]-2-oxoethyl]amino]-2-oxo-1-(2-pyridylmethyl)ethyl]-2-propenamideYield 83.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of (2S)-2-amino-N-[2-[4-(4-chlorophenyl)-1-piperazinyl]-2-oxoethyl]-3-(2-pyridyl)propanamide (29 g) and 4-chlorocinnamic acid (13.1 g) in N,N-dimethylformamide (230 ml) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (15.2 g) and N-hydroxybenzotriazole (10.7 g) at 0° C. The mixture was stirred at room temperature for 20 hours. The reaction mixture was poured into ice-cold saturated aqueous sodium hydrogencarbonate solution and the resulting solid was collected by filtration. The solid was washed successively with saturated aqueous sodium hydrogencarbonate solution and water. The solid was crystallized from water:ethanol (1:9 (v/v)) to give the title compound (34 g) as crystals.

Workup

  1. additionThe reaction mixture was poured into ice-cold saturated aqueous sodium hydrogencarbonate solution
  2. filtrationthe resulting solid was collected by filtration
  3. washThe solid was washed successively with saturated aqueous sodium hydrogencarbonate solution and water
  4. customThe solid was crystallized from water:ethanol (1:9 (v/v))

Sources & evidence

ORD record
ord-ea95eb61164e43aa92f298a7288abb86
Source dataset
uspto-grants-2004_11
Patent number
US06825200B1

Reaction notes

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