Diisopropylethylamine → Phenyl[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]methanone

HRID 2244268Notes

Reaction equation

HRID 2244268 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[NH:7][CH2:6][C:5]=12.C(N(CC)C(C)C)(C)C.[C:24]([C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl>[C:25]1([C:24]([C:32]2[CH:33]=[CH:34][C:35]([C:36]([N:7]3[C:8]4[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=4[CH2:10][N:4]4[CH:3]=[CH:2][CH:1]=[C:5]4[CH2:6]3)=[O:37])=[CH:39][CH:40]=2)=[O:31])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 129121414-Benzoylbenzoyl chlorideHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine

Product 1

HCID 22405323Phenyl[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]methanoneYield 101.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To solution of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.807 g, 4.38 mmol) in dry dichloromethane (20 mL) cooled in an ice bath was added N,N-diisopropylethyl amine (1.14 mL). The solution was treated dropwise with a suspension of 4-benzoylbenzoyl chloride (prepared from 3 mmol of 4-benzoylbenzoic acid and oxalyl chloride) in 8 mL of dichloromethane. The solution was stirred overnight at room temperature, diluted with dichloromethane, washed with water, 1 N hydrochloric acid, saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was flash chromatographed over silica gel Merck-60 with a solvent gradient of 5 to 20% of ethyl acetate in hexane to provide the title compound (1.2 g) as a crystalline solid.

Workup

  1. washwashed with water, 1 N hydrochloric acid, saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated to dryness
  4. customchromatographed over silica gel Merck-60 with a solvent gradient of 5 to 20% of ethyl acetate in hexane

Sources & evidence

ORD record
ord-6101df4af46143d48bd278f5c57bf997
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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