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

HRID 1598211Notes

Reaction equation

HRID 1598211 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 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, m.p. 162°-188° C. (amorphous)

Workup

  1. washThe reaction mixture is washed with water, 2N 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

Sources & evidence

ORD record
ord-f7c1de745b4b42138ea5a208bde0b222
Source dataset
uspto-grants-1998_04
Patent number
US05736540

Reaction notes

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