Benzoyl chloride → HCID 54704603, compound

HRID 2214658Notes

Reaction equation

HRID 2214658 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:12]=[C:13]([CH:34]=[CH:35][C:36]=1[Cl:37])[CH2:14][N:15]([CH3:33])[C:16]([C:18]1[CH2:19][N:20]([CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[C:21](=[O:24])[C:22]=1[OH:23])=[O:17]>ClCCl.N1C=CC=CC=1.ClCCl>[Cl:10][C:11]1[CH:12]=[C:13]([CH:34]=[CH:35][C:36]=1[Cl:37])[CH2:14][N:15]([CH3:33])[C:16]([C:18]1[CH2:19][N:20]([CH2:25][CH2:26][N:27]2[CH2:28][CH2:29][N:30]([C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:31][CH2:32]2)[C:21](=[O:24])[C:22]=1[OH:23])=[O:17]

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 54704660HCID 54704660, compound

Product 1

HCID 54704603HCID 54704603, compoundYield 20.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21875418Pyridine methylene chlorideSolvent

Procedure

To a solution of benzoyl chloride (0.023 mL, 0.23 mmol) in dichloromethane (1 mL) cooled to 0° C. was added dropwise a solution of 4-hydroxy-5-oxo-1-(2-piperazin-1-yl-ethyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid (3,4-dichloro-benzyl)-methyl-amide (0.10 g, 0.20 mmol) in pyridine/dichloromethane (4 mL, 1:1). The resulting mixture was stirred at room temp 18 h and quenched with 1N HCl. The organic phase was washed with 1N HCl (3 times). The aqueous washings were combined and purified by preparative HPLC (C18, ODS-A, S-75 μm, 30% acetonitrile/water/0.5% TFA) to give the title compound as a white powder (0.0215 g, 20% yield). HRMS (M+H) calcd for C26H29N4Cl2O4: 531.1566; found: 531.1563.

Workup

  1. customquenched with 1N HCl
  2. washThe organic phase was washed with 1N HCl (3 times)
  3. custompurified by preparative HPLC (C18, ODS-A, S-75 μm, 30% acetonitrile/water/0.5% TFA)

Sources & evidence

ORD record
ord-f634001508bb47329e0adbdf0ed69d31
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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