Triethylamine → N-[4(5H-Pyrrolo[2,1-c][1,4]benzodiazepin10(11H)-ylcarbonyl)phenyl]-2-methylbenzeneacetamide

HRID 55163

Reaction equation

HRID 55163 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9](Cl)=[O:10].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:9](=[O:10])[CH2:8][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[CH3:1])=[CH:41][CH:40]=3)=[O:25])[CH2:27][C:28]=12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2760632o-Tolyl-acetyl chlorideHCID 1082828010,11-dihydro-10(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Product 1

HCID 21837119N-[4(5H-Pyrrolo[2,1-c][1,4]benzodiazepin10(11H)-ylcarbonyl)phenyl]-2-methylbenzeneacetamideYield 53.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 0.334 g of 2-methylphenylacetyl 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, NaCHO3, and brine. The reaction mixture is dried with Na2SO4, filtered through a pad of hydrous magnesium silicate 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 acetate to give 0.385 g of the desired product as white crystals, m.p. 198°-200° C.

Workup

  1. stirringstirring
  2. waitcontinued for 72 hours at room temperature
  3. washwashed with water, 2N citric acid, NaCHO3, and brine
  4. dry with materialThe reaction mixture is dried with Na2SO4
  5. filtrationfiltered through a pad of hydrous magnesium silicate
  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 acetate

Sources & evidence

ORD record
ord-b5001a661b274ed39ffe674a6a68eb56
Source dataset
uspto-grants-1997_04
Patent number
US05624923

Linked notes

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