Triethylamine → 4-[(6,7-Dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepin-5-ylcarbonyl)phenyl]-2-methyl-benzamide

HRID 55197Notes

Reaction equation

HRID 55197 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:13](CC)CC)C.N[C:19]1[CH:40]=[CH:39][C:22]([C:23]([N:25]2[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[N:29]3[CH:36]=[CH:37][CH:38]=[C:28]3[CH2:27][CH2:26]2)=[O:24])=[CH:21][CH:20]=1>C(Cl)Cl>[CH:35]1[C:30]2[N:29]3[CH:36]=[CH:37][CH:38]=[C:28]3[CH2:27][CH2:26][N:25]([C:23]([C:22]3[CH:21]=[CH:20][CH:19]=[CH:40][C:39]=3[C:9]3[CH:8]=[CH:7][C:3]([C:4]([NH2:13])=[O:5])=[C:2]([CH3:1])[CH:10]=3)=[O:24])[C:31]=2[CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 702762-Methylbenzoyl chlorideHCID 218371566,7-Dihydro-5-(4-aminobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepine

Product 1

HCID 867507754-[(6,7-Dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepin-5-ylcarbonyl)phenyl]-2-methyl-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5 mmol of 2-methylbenzoyl chloride in 10 ml of methylene chloride is added 7 mmol of triethylamine and 5 mmol of 6,7-dihydro-5-(4-aminobenzoyl)-5H-pyrrolo[1,2-a]-[1,5]benzodiazepine. The reaction mixture is washed with water, 2M citric acid, NaHCO3, and brine. The organic layer is dried with Na2SO4, filtered and evaporated in vacuo to give a solid which is purified by flash chromatography on silica gel to give the desired product as a solid; mass spectrum (CI): 422 (M+H).

Workup

  1. washThe reaction mixture is washed with water, 2M citric acid, NaHCO3, and brine
  2. dry with materialThe organic layer 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

Sources & evidence

ORD record
ord-7c48570758114929aa45ec35022e96be
Source dataset
uspto-grants-1997_04
Patent number
US05624923

Reaction notes

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