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

HRID 1739979Notes

Reaction equation

HRID 1739979 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-2ae4c5db79024398b9f2a29afa466237
Source dataset
uspto-grants-1999_10
Patent number
US05968930

Reaction notes

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