Triethylamine → N-[4-(5H-Pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-3-methylbenzo[b]thiophene-2-acetamide

HRID 1456067

Reaction equation

HRID 1456067 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[S:4][C:3]=1[CH2:11][C:12](Cl)=[O:13].C(N(CC)CC)C.[NH2:22][C:23]1[CH:44]=[CH:43][C:26]([C:27]([N:29]2[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[CH2:33][N:32]3[CH:40]=[CH:41][CH:42]=[C:31]3[CH2:30]2)=[O:28])=[CH:25][CH:24]=1.CN(C1C=CC=CN=1)C>C(Cl)Cl>[CH:42]1[CH:41]=[CH:40][N:32]2[CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[N:29]([C:27]([C:26]3[CH:25]=[CH:24][C:23]([NH:22][C:12](=[O:13])[CH2:11][C:3]4[S:4][C:5]5[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=5[C:2]=4[CH3:1])=[CH:44][CH:43]=3)=[O:28])[CH2:30][C:31]=12

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 218852-DimethylaminopyridineHCID 1082828010,11-dihydro-10(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepineHCID 218370343-Methylbenzo[b]thiophene-2-acetyl chloride2×

Product 1

HCID 15340671N-[4-(5H-Pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-3-methylbenzo[b]thiophene-2-acetamideYield 39.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 0.445 g of 3-methylbenzo[b]thiophene-2-acetyl chloride in 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. An additional 0.445 g of 3-methylbenzo[b]thiophene-2-acetyl chloride, 0.346 g of triethylamine and 30 mg of dimethylaminopyridine is added and stirring continued for an additional 18 hours. The reaction mixture is diluted with 45 ml of methylene chloride and washed with water, 2N citric acid, 1M NaHCO3, and brine. The reaction mixture is dried with Na2 SO4, filtered and evaporated in vacuo to give a solid which is purified by flash chromatography using 1:1 ethyl acetate-hexane to give 0.320 g of the desired product as a yellow foam.

Workup

  1. stirringstirring
  2. waitcontinued for 72 hours at room temperature
  3. stirringstirring
  4. waitcontinued for an additional 18 hours
  5. washwashed with water, 2N citric acid, 1M NaHCO3, and brine
  6. customThe reaction mixture is dried with Na2 SO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customto give a solid which
  10. customis purified by flash chromatography

Sources & evidence

ORD record
ord-d6366ed4b3614b528e66fa53a55499ac
Source dataset
uspto-grants-1998_12
Patent number
US05843944

Linked notes

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