Triethylamine → N-[4-(5H-Pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepin-4(10H)-ylcarbonyl)phenyl]-2-methylbenzamide

HRID 1456108Notes

Reaction equation

HRID 1456108 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[CH:32]=[CH:33][S: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>[S:34]1[C:30]2[CH2:29][N:28]3[CH:35]=[CH:36][CH:37]=[C:27]3[CH2:26][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])[C:31]=2[CH:32]=[CH:33]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 702762-Methylbenzoyl chlorideHCID 218369774,10-Dihydro-4-(4-aminobenzoyl)-5H-pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine

Product 1

HCID 15340675N-[4-(5H-Pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepin-4(10H)-ylcarbonyl)phenyl]-2-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3 mmol of 2-methylbenzoyl chloride in 10 ml of methylene chloride is added 5 mmol of triethylamine and 3 mmol of 4,10-dihydro-4-(4-aminobenzoyl)-5H-pyrrolo-[1,2-a]thieno[3,2-e][1,4]diazepine. The mixture is stirred for 5 hours. The reaction mixture is washed with water, 2N citric acid, NaHCO3, and brine. The reaction mixture is dried with Na 2SO4 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, m.p. 162°-188° C. (amorphous)

Workup

  1. washThe reaction mixture is washed with water, 2N citric acid, NaHCO3, and brine
  2. customThe reaction mixture is dried with Na
  3. filtration2SO4 filtered
  4. customevaporated in vacuo
  5. customto give a solid which
  6. customis purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-81a3733072594c428574175275ad1333
Source dataset
uspto-grants-1998_12
Patent number
US05843944

Reaction notes

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