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

HRID 1956348Notes

Reaction equation

HRID 1956348 reaction equation
[C:1]([C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:18]1[CH:19]=[CH:20][N:21]2[CH2:27][C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[NH:24][CH2:23][C:22]=12.C(N(CC)CC)C>C(Cl)Cl.C(Cl)(Cl)Cl>[C:1]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([N:24]2[C:25]3[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=3[CH2:27][N:21]3[CH:20]=[CH:19][CH:18]=[C:22]3[CH2:23]2)=[O:14])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 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 84.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.16 g of 4-(benzoyl)benzoyl chloride (Reference Example 36) and 1.0 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 30 ml of methylene chloride containing 7 ml of triethylamine is stirred under nitrogen atmosphere for 16 hours. The reaction mixture is diluted with 50 ml of chloroform and washed with 2N HCl, water, saturated NaHCO3 and water. The organic layer is dried (Na2SO4) and columned on silica gel by elution with 7:1 to 3:1 ethyl acetate:hexane to give 1.8 g of the desired product as a solid. M+H 393.2; M+Na 415.2.

Workup

  1. washwashed with 2N HCl, water, saturated NaHCO3 and water
  2. dry with materialThe organic layer is dried (Na2SO4)
  3. washcolumned on silica gel by elution with 7:1 to 3:1 ethyl acetate

Sources & evidence

ORD record
ord-626fef12eabc4f5f961ff3c2cb209f23
Source dataset
uspto-grants-1998_07
Patent number
US05780471

Reaction notes

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