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Triethylamine → N-[4-(5H-Pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-2-ethoxybenzamide

HRID 3509
Notes
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Reaction equation

HRID 3509 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7])[CH3:2].C(N(CC)CC)C.[NH2:20][C:21]1[CH:42]=[CH:41][C:24]([C:25]([N:27]2[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=3[CH2:31][N:30]3[CH:38]=[CH:39][CH:40]=[C:29]3[CH2:28]2)=[O:26])=[CH:23][CH:22]=1>C(Cl)Cl>[CH:40]1[CH:39]=[CH:38][N:30]2[CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[N:27]([C:25]([C:24]3[CH:23]=[CH:22][C:21]([NH:20][C:6](=[O:7])[C:5]4[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=4[O:3][CH2:1][CH3:2])=[CH:42][CH:41]=3)=[O:26])[CH2:28][C:29]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 30163972-Ethoxybenzoyl chlorideHCID 1082828010,11-dihydro-10(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Product 1

HCID 21837089N-[4-(5H-Pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-2-ethoxybenzamideYield 100.5%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

To a stirred solution of 0.362 g of 2-ethoxybenzoyl chloride 5 ml of methylene chloride is added 0.346 g of triethylamine at 0° C. After stirring for 3 minutes, 0,500 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added and stirring continued for 72 hours at room temperature. The reaction mixture is diluted with 45 ml of methylene chloride and washed with water, 2N citric acid, NaHCO3, and brine. The reaction mixture is dried with Na2SO4, filtered and evaporated in vacuo to give a solid which is purified by flash chromatography using 1:1 ethyl acetate-hexane to give 0.890 g of solid which is crystallized from ethyl acetate to give 0.540 g of the desired product as a white solid, m.p. 160°-176° C.

Workup

  1. stirringstirring
  2. waitcontinued for 72 hours at room temperature
  3. washwashed with water, 2N citric acid, NaHCO3, and brine
  4. dry with materialThe reaction mixture is dried with Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give a solid which
  8. customis purified by flash chromatography

Sources & evidence

ORD record
ord-9bacf453371f41c29a68bca6e3de295d
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05733905

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes