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

HRID 2246834Notes

Reaction equation

HRID 2246834 reaction equation
[Cl:1][C:2]([Cl:7])([Cl:6])[C:3](Cl)=[O:4].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:21]=[CH:20][C:19]([C:22]([N:24]2[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[CH2:28][N:27]3[CH:35]=[CH:36][CH:37]=[C:26]3[CH2:25]2)=[O:23])=[CH:18][CH:17]=1.C(N(CC)C(C)C)(C)C>ClCCl>[Cl:1][C:2]([Cl:7])([Cl:6])[C:3]([C:35]1[N:27]2[C:26]([CH2:25][N:24]([C:22]([C:19]3[CH:20]=[CH:21][C:16]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[O:9][CH3:8])=[CH:17][CH:18]=3)=[O:23])[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[CH2:28]2)=[CH:37][CH:36]=1)=[O:4]

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 10200666(2'-methoxy-biphenyl-4-yl)-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-methanone

Product 1

HCID 160384072,2,2-trichloro-1-{10-[(2'-methoxy-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanoneYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trichloroacetyl chloride (2.63 mL, 23.6 mmol) was added dropwise over five minutes to a solution of (2′-methoxy-biphenyl-4-yl)-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-methanone (3.0 g, 7.60 mmol) and N,N-diisopropylethyl amine (2.65 mL, 15.2 mmol) in dichloromethane (60 mL). The reaction was stirred under nitrogen at room temperature overnight and then quenched with water. The organic layer was washed with 0.1N hydrochloric acid and water, dried over anhydrous magnesium sulfate, filtered and concentrated to an oil. The oil was purified by flash chromatography over silica gel Merck-60 using a 0-5% gradient of ethyl acetate in dichloromethane to give the title compound (2.34 g) as a yellow foam.

Workup

  1. customquenched with water
  2. washThe organic layer was washed with 0.1N hydrochloric acid and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to an oil
  6. customThe oil was purified by flash chromatography over silica gel Merck-60

Sources & evidence

ORD record
ord-cd96679e7bf347b0ad9a7c67d1e0fbad
Source dataset
uspto-grants-2010_03
Patent number
US07687623B2

Reaction notes

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