Triethylamine → N-[4-(5H,11H-Benzo[e]pyrrolo[1,2-a][1,4]diazepine-10-carbonyl)-phenyl]-2-methylsulfanyl-benzamide

HRID 1459490Notes

Reaction equation

HRID 1459490 reaction equation
[CH3:1][S:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5](Cl)=[O:6].C(N(CC)CC)C.[NH2:19][C:20]1[CH:41]=[CH:40][C:23]([C:24]([N:26]2[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=3[CH2:30][N:29]3[CH:37]=[CH:38][CH:39]=[C:28]3[CH2:27]2)=[O:25])=[CH:22][CH:21]=1>C(Cl)Cl>[CH:39]1[CH:38]=[CH:37][N:29]2[CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[N:26]([C:24]([C:23]3[CH:22]=[CH:21][C:20]([NH:19][C:5](=[O:6])[C:4]4[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=4[S:2][CH3:1])=[CH:41][CH:40]=3)=[O:25])[CH2:27][C:28]=12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1082828010,11-dihydro-10(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepineHCID 125767982-(Methylsulfanyl)benzoyl chloride

Product 1

HCID 21837162N-[4-(5H,11H-Benzo[e]pyrrolo[1,2-a][1,4]diazepine-10-carbonyl)-phenyl]-2-methylsulfanyl-benzamideYield 64.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 0.364 g of 2-(methylthio)benzoyl 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 a solid which is crystallized from ethyl alcohol to give 0.480 g of the desired product as a white solid, m.p. 171°-174° 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
  9. customto give a solid which
  10. customis crystallized from ethyl alcohol

Sources & evidence

ORD record
ord-20639a82a0e340bf9168cdc08e3c6919
Source dataset
uspto-grants-1998_12
Patent number
US05854237

Reaction notes

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