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

HRID 1740036
Notes
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Reaction equation

HRID 1740036 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6344
Dichloromethane
Solvent
2×

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. concentrationThe filtrate is concentrated
  3. dissolutionthe residue (4.0 g) dissolved in dichloromethane
  4. filtrationagain filtered through a pad of hydrous magnesium silicate
  5. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-8fe4d0627d12489882c4d40852f5e6d6
Source dataset
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05968930

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes