Trichloroacetyl chloride → 2,2,2-Trichloro-1-{10-[(2-methoxy-2'-methyl-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone

HRID 639237Notes

Reaction equation

HRID 639237 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([N:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][N:14]3[CH:22]=[CH:23][CH:24]=[C:13]3[CH2:12]2)=[O:10])[CH:6]=[CH:5][C:4]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:31].C(N(CC)CC)C.[Cl:39][C:40]([Cl:45])([Cl:44])[C:41](Cl)=[O:42].C(OCC)(=O)C>ClCCl.C(Cl)(Cl)Cl>[Cl:39][C:40]([Cl:45])([Cl:44])[C:41]([C:22]1[N:14]2[C:13]([CH2:12][N:11]([C:9]([C:7]3[CH:6]=[CH:5][C:4]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[CH3:31])=[C:3]([O:2][CH3:1])[CH:8]=3)=[O:10])[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15]2)=[CH:24][CH:23]=1)=[O:42]

Participants

7

Reactant 4

HCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 6867947010-[(2-Methoxy-2'-methyl-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Product 1

HCID 160388252,2,2-Trichloro-1-{10-[(2-methoxy-2'-methyl-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanoneYield 87.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 10-[(2-methoxy-2′-methyl-1,1′-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine of Step E (21 mmol) and triethylamine (43 mmol) in anhydrous dichloromethane (45 mL) was cooled in an ice bath. To the stirred solution was added, dropwise, trichloroacetyl chloride (65 mmol). The mixture was allowed to stir at ambient temperature for 72 hours, then was washed with 0.1 N hydrochloric acid and brine, and dried over anhydrous sodium sulfate. Evaporation yielded a foam that solidified by heating with ethyl acetate and chloroform to provide 10.2 g (85%) of the title compound as a white solid, m.p. 221-222° C. MS [(+)ESI, m/z]: 553 [M+H]+

Workup

  1. additionTo the stirred solution was added
  2. washwas washed with 0.1 N hydrochloric acid and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customEvaporation
  5. customyielded a foam that solidified

Sources & evidence

ORD record
ord-f0d1bddc9dba46c7981cc08e749090af
Source dataset
uspto-grants-2010_04
Patent number
US07691848B2

Reaction notes

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