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

HRID 1739871Notes

Reaction equation

HRID 1739871 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1.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][C:2]([Cl:1])=[CH:3][C:4]=4[O:11][CH3:12])=[CH:42][CH:41]=3)=[O:26])[CH2:28][C:29]=12

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 1082828010,11-dihydro-10(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepineHCID 221424504-Chloro-2-methoxybenzoyl chloride2×

Product 1

HCID 10528416N-[4-(5H-Pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)ylcarbonyl)phenyl]-4-chloro-2-methoxybenzamideYield 41.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 0.406 g of 4-chloro-2-methoxybenzoyl chloride in 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 18 hours at room temperature. An additional 0.406 g of 4-chloro-2-methoxybenzoyl chloride and 0.346 g of triethylamine is added and stirring is continued for 2 hours. The reaction mixture is diluted with 45 ml of methylene chloride and washed with water, 2N citric acid, 1M NaHCO3, and brine. The reaction mixture is dried with Na2SO4, filtered and evaporated in vacuo to give a residue which is purified by flash chromatography using 1:1 ethyl acetate-hexane to give a solid which is crystallized from ethyl acetate to give 0.320 g of the desired product as a white crystals, m.p. 222-224° C.

Workup

  1. stirringstirring
  2. waitcontinued for 18 hours at room temperature
  3. stirringstirring
  4. waitis continued for 2 hours
  5. washwashed with water, 2N citric acid, 1M NaHCO3, and brine
  6. dry with materialThe reaction mixture is dried with Na2SO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customto give a residue which
  10. customis purified by flash chromatography
  11. customto give a solid which
  12. customis crystallized from ethyl acetate

Sources & evidence

ORD record
ord-a35f2c46cac54a508ee2747aff6ac894
Source dataset
uspto-grants-1999_10
Patent number
US05968937

Reaction notes

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