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

HRID 440030Notes

Reaction equation

HRID 440030 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.[CH3:24][C:25]1[CH:43]=[CH:42][CH:41]=[CH:40][C:26]=1[C:27]([NH:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][C:31]=1[Cl:39])=[O:28]>ClCCl>[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[N:7]([C:34]([C:33]3[CH:37]=[CH:38][C:30]([NH:29][C:27](=[O:28])[C:26]4[CH:40]=[CH:41][CH:42]=[CH:43][C:25]=4[CH3:24])=[C:31]([Cl:39])[CH:32]=3)=[O:35])[CH2:6][C:5]=12

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepineHCID 218371014-[(2-Methylbenzoyl)amino]-3-chlorobenzoyl chloride

Product 1

HCID 21837082N-[4-(5H-Pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)ylcarbonyl)-2-chlorophenyl]-2-methylbenzamideYield 106%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 1.38 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 1.11 g of N,N-diisopropylethylamine in 50 ml of dichloromethane is added 2.61 g of 4-[(2-methylbenzoyl)amino]-3-chlorobenzoyl chloride in 25 ml of dichloromethane. The mixture is stirred at room temperature overnight and then washed with H2O and saturated NaHCO3. The organic layer is dried (Na2SO4) and passed through a pad of hydrous magnesium silicate. The filtrate is concentrated, the residue (4.0 g) dissolved in dichloromethane and again filtered through a pad of hydrous magnesium silicate. The filtrate is evaporated to give the product as a glass (3.62 g). A 1.8 g sample of the glass is crystallized from ethyl acetate to give 1.4 g of crystals, m.p. 176°-178° C.

Workup

  1. washwashed with H2O and saturated NaHCO3
  2. dry with materialThe organic layer is dried (Na2SO4)
  3. concentrationThe filtrate is concentrated
  4. dissolutionthe residue (4.0 g) dissolved in dichloromethane
  5. filtrationagain filtered through a pad of hydrous magnesium silicate
  6. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-0d7c10c166c4419eb6eb23296395a6be
Source dataset
uspto-grants-1996_05
Patent number
US05516774

Reaction notes

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