2-Methylbenzoyl chloride → N-[4-(5H-Pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)ylcarbonyl)-2-methylphenyl]-2-methylbenzamide

HRID 3518

Reaction equation

HRID 3518 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]3[CH:19]=[CH:20][CH:21]=[C:10]3[CH2:9]2)=[O:7])=[CH:4][C:3]=1[CH3:24].C(N(CC)C(C)C)(C)C.[CH3:34][C:35]1[CH:43]=[CH:42][CH:41]=[CH:40][C:36]=1[C:37](Cl)=[O:38]>C(Cl)Cl>[CH:21]1[CH:20]=[CH:19][N:11]2[CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:8]([C:6]([C:5]3[CH:22]=[CH:23][C:2]([NH:1][C:37](=[O:38])[C:36]4[CH:40]=[CH:41][CH:42]=[CH:43][C:35]=4[CH3:34])=[C:3]([CH3:24])[CH:4]=3)=[O:7])[CH2:9][C:10]=12

Participants

5

Reactant 3

HCID 702762-Methylbenzoyl chlorideHCID 81531DiisopropylethylamineHCID 1068697510,11-Dihydro-10-(4-amino-3-methylbenzoyl)-5H-Pyrrolo[2,1-c][1,4]benzodiazepine

Product 1

HCID 21837166N-[4-(5H-Pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)ylcarbonyl)-2-methylphenyl]-2-methylbenzamideYield 65.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.83 g of 10,11-dihydro-10-(4-amino-3-methylbenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 0.5 g of N,N-diisopropylethylamine and 0.6 g of 2-methylbenzoyl chloride in 50 ml of methylene chloride is stirred at room temperature for 18 hours. The reaction mixture is washed with water, the organic layer dried with Na2SO4 and passed through a pad of hydrous magnesium silicate. Hexane is added at the boil to give 0.75 g of a solid which is crystallized from methylene chloride-hexane to give 0.61 g of the desired product, m.p. 125°-130° C.

Workup

  1. washThe reaction mixture is washed with water
  2. dry with materialthe organic layer dried with Na2SO4
  3. additionHexane is added at the boil

Sources & evidence

ORD record
ord-a0865d39ece04d7ca18701901cb148a2
Source dataset
uspto-grants-1998_03
Patent number
US05733905

Linked notes

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