Triethylamine → N-[4-(4H-Furo[2,3-e]pyrrolo[1,2-a][1,4]-diazepin-10(9H)-ylcarbonyl)phenyl]-2-methyl benzamide

HRID 1459516Notes

Reaction equation

HRID 1459516 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].C(N(CC)CC)C.[NH2:18][C:19]1[CH:39]=[CH:38][C:22]([C:23]([N:25]2[C:31]3[O:32][CH:33]=[CH:34][C:30]=3[CH2:29][N:28]3[CH:35]=[CH:36][CH:37]=[C:27]3[CH2:26]2)=[O:24])=[CH:21][CH:20]=1>C(Cl)Cl>[O:32]1[C:31]2[N:25]([C:23]([C:22]3[CH:21]=[CH:20][C:19]([NH:18][C:4](=[O:5])[C:3]4[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=4[CH3:1])=[CH:39][CH:38]=3)=[O:24])[CH2:26][C:27]3[N:28]([CH:35]=[CH:36][CH:37]=3)[CH2:29][C:30]=2[CH:34]=[CH:33]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 702762-Methylbenzoyl chlorideHCID 540426559,10-Dihydro-10-(4-aminobenzoyl)-4H-furo[2,3-e]pyrrolo[1,2-a][1,4]diazepine

Product 1

HCID 21837211N-[4-(4H-Furo[2,3-e]pyrrolo[1,2-a][1,4]-diazepin-10(9H)-ylcarbonyl)phenyl]-2-methyl benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1.1 mmol of 2-methylbenzoyl chloride in 10 ml of methylene chloride is added 1.5 mmol of triethylamine. To the mixture is added 1.1 mmol of 9,10-dihydro-10-(4-aminobenzoyl)-4H-furo-[2,3-e]pyrrolo[1,2-a][1,4]diazepine and the mixture is stirred for 5 hours. The reaction mixture is washed with water, 1N 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 on silica gel with ethyl acetate-hexane as solvent to give the desired product as a solid.

Workup

  1. washThe reaction mixture is washed with water, 1N citric acid, NaHCO3, and brine
  2. dry with materialThe reaction mixture is dried with Na2SO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customto give a solid which
  6. customis purified by flash chromatography on silica gel with ethyl acetate-hexane as solvent

Sources & evidence

ORD record
ord-ed4d87221e704424abe79007aa67cf34
Source dataset
uspto-grants-1998_12
Patent number
US05854237

Reaction notes

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