1-Hydroxybenzotriazole → 5-Chloro-N-[(1S)-2-[[2-[4-(4-chlorophenyl)-1-piperazinyl]-2-oxoethyl]amino]-2-oxo-1-(2-pyridylmethyl)ethyl]-1-benzofuran-2-carboxamide

HRID 2416643Notes

Reaction equation

HRID 2416643 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:31]=[CH:32][C:33]2[O:37][C:36]([C:38](O)=[O:39])=[CH:35][C:34]=2[CH:41]=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]2[O:37][C:36]([C:38]([NH:1][C@@H:2]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[C:3]([NH:5][CH2:6][C:7]([N:9]3[CH2:10][CH2:11][N:12]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=4)[CH2:13][CH2:14]3)=[O:8])=[O:4])=[O:39])=[CH:35][C:34]=2[CH:41]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 9378385-Chloro-1-benzofuran-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69933682HCID 69933682, compound

Product 1

HCID 98945165-Chloro-N-[(1S)-2-[[2-[4-(4-chlorophenyl)-1-piperazinyl]-2-oxoethyl]amino]-2-oxo-1-(2-pyridylmethyl)ethyl]-1-benzofuran-2-carboxamideYield 88.5%

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 (18 g) and 5-chloro-1-benzofuran-2-carboxylic acid (8.8 g) in N,N-dimethyl-formamide (180 ml) were added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (9.44 g) and N-hydroxybenzotriazole (6.66 g) at 0° C. The mixture was stirred at room temperature for 14 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 (23 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-db6cf40fedda4658941602b6027c89bf
Source dataset
uspto-grants-2004_11
Patent number
US06825200B1

Reaction notes

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