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

HRID 2246846Notes

Reaction equation

HRID 2246846 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[CH3:29])=[C:19]([CH3:30])[CH:18]=3)=[O:16])[CH2:6][C:5]=12.C(N(CC)CC)C.[Cl:38][C:39]([Cl:44])([Cl:43])[C:40](Cl)=[O:41]>ClCCl>[Cl:38][C:39]([Cl:44])([Cl:43])[C:40]([C:3]1[N:4]2[C:5]([CH2:6][N:7]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[CH3:29])=[C:19]([CH3:30])[CH:18]=3)=[O:16])[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10]2)=[CH:1][CH:2]=1)=[O:41]

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 68680291(10,11-Dihydro-5H-pyrrolo[2,1-c](1,4]benzodiazepin-10-yl)-(2,2'-dimethyl-biphenyl-4-yl)-methanone

Product 1

HCID 160384712,2,2-Trichloro-1-{10-[(2,2'-dimethyl-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-10-yl)-(2,2′-dimethyl-biphenyl-4-yl)-methanone of Step C (8.38 mmol) and triethylamine (16.76 mmol) in dichloromethane (30 mL) at −5° C. was added, rapidly dropwise, trichloroacetyl chloride (25 mmol). The mixture was allowed to stir and warm to room temperature overnight. The mixture was washed with 0.1N hydrochloric acid and dilute brine, then dried over anhydrous sodium sulfate, and evaporated to leave a light green oil. The compound was purified by filtration over a plug of Merck silica gel-60 eluting with dichloromethane and then treated with hot ethyl acetate/hexane (3/1) to yield a light yellow crystalline solid, m.p. 212-214° C.

Workup

  1. washThe mixture was washed with 0.1N hydrochloric acid and dilute brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated
  4. customto leave a light green oil
  5. filtrationThe compound was purified by filtration over a plug of Merck silica gel-60 eluting with dichloromethane
  6. additiontreated with hot ethyl acetate/hexane (3/1)
  7. customto yield a light yellow crystalline solid, m.p. 212-214° C.

Sources & evidence

ORD record
ord-4a4795067cad41c89a6d361ea2e0f7bc
Source dataset
uspto-grants-2010_03
Patent number
US07687623B2

Reaction notes

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