Triethylamine → 10-[4-[[(2-Chlorophenyl)sulfonyl]amino]benzoyl]-10,11-dihydro-5H-pyrrolo(2,1-c][1,4]benzodiazepine

HRID 1456134Notes

Reaction equation

HRID 1456134 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].[NH2:12][C:13]1[CH:34]=[CH:33][C:16]([C:17]([N:19]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[CH2:23][N:22]3[CH:30]=[CH:31][CH:32]=[C:21]3[CH2:20]2)=[O:18])=[CH:15][CH:14]=1.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:12][C:13]1[CH:34]=[CH:33][C:16]([C:17]([N:19]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[CH2:23][N:22]3[CH:30]=[CH:31][CH:32]=[C:21]3[CH2:20]2)=[O:18])=[CH:15][CH:14]=1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 761872-Chlorobenzenesulfonyl chlorideHCID 1082828010,11-dihydro-10(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Product 1

HCID 1534067710-[4-[[(2-Chlorophenyl)sulfonyl]amino]benzoyl]-10,11-dihydro-5H-pyrrolo(2,1-c][1,4]benzodiazepineYield 20.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.418 g of 2-chlorobenzenesulfonyl chloride in 5 ml of dichloromethane, cooled to 0° C. is added 0.50 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine and 0.346 μl of triethylamine. The mixture is stirred at room temperature overnight and diluted with 50 ml of dichloromethane. The mixture is washed with 20 ml each of H2O, 2N citric acid, 1M NaHCO3, brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate and the filtrate concentrated to dryness. The residue is chromatographed on thick layer silica gel plates (4) with the solvent ethyl acetate-hexane (1:1) to give a solid. Crystallization from ethyl acetate gives 0.165 g of white crystals, m.p. 206°-210° C.

Workup

  1. washThe mixture is washed with 20 ml each of H2O, 2N citric acid, 1M NaHCO3, brine
  2. dry with materialdried (Na2SO4)
  3. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  4. concentrationthe filtrate concentrated to dryness
  5. customThe residue is chromatographed on thick layer silica gel plates (4) with the solvent ethyl acetate-hexane (1:1)
  6. customto give a solid
  7. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-172ddf877be1489ca3ef90b8859996a1
Source dataset
uspto-grants-1998_12
Patent number
US05843944

Reaction notes

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