Reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]3[CH:19]=[CH:20][CH:21]=[C:10]3[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:31][CH2:32][C:33](Cl)=[O:34]>C(Cl)Cl.CN(C1C=CC=CN=1)C>[Cl:31][CH2:32][C:33]([NH:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]3[CH:19]=[CH:20][CH:21]=[C:10]3[CH2:9]2)=[O:7])=[CH:4][CH:3]=1)=[O:34]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of 0.91 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 10 ml of methylene chloride is added 0.46 g of triethylamine and 36 mg of dimethylamino-pyridine followed by the slow addition of 0.42 g of chloroacetyl chloride in 5 ml of methylene chloride. The resulting mixture is stirred at room temperature for 3 hours then partitioned with 10 ml of 50% NaHCO3 and the methylene chloride evaporated in vacuo. The remaining suspension is filtered, washed with 50% NaHCO3, H2O, EtOAc (2×2 ml), ether (2×5 ml) and dried in vacuo to give 1.14 g of beige solid. MS(CI): 380(M+H) .
Workup
- customthen partitioned with 10 ml of 50% NaHCO3
- customthe methylene chloride evaporated in vacuo
- filtrationThe remaining suspension is filtered
- washwashed with 50% NaHCO3, H2O, EtOAc (2×2 ml), ether (2×5 ml)
- customdried in vacuo
Sources & evidence
- ORD record
- ord-e06cdb4daf3043c0a42a16dac439e925
- Source dataset
- uspto-grants-1996_05
- Patent number
- US05516774
Linked notes
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