Acetonitrile → N-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-ylmethyl)-N-(2-pyridin-3-ylethyl)benzenesulfonamide

HRID 1504138Notes

Reaction equation

HRID 1504138 reaction equation
C(N(CC)CC)C.C(#N)C.[CH2:11]([N:13]1[C:19](=[O:20])[C:18]([CH3:22])([CH3:21])[C:17](=[O:23])[N:16]([CH3:24])[C:15]2[CH:25]=[C:26]([CH2:29][NH:30][CH2:31][CH2:32][C:33]3[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=3)[CH:27]=[CH:28][C:14]1=2)[CH3:12].[C:39]1([S:45](Cl)(=[O:47])=[O:46])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>O>[CH2:11]([N:13]1[C:19](=[O:20])[C:18]([CH3:22])([CH3:21])[C:17](=[O:23])[N:16]([CH3:24])[C:15]2[CH:25]=[C:26]([CH2:29][N:30]([CH2:31][CH2:32][C:33]3[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=3)[S:45]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)(=[O:47])=[O:46])[CH:27]=[CH:28][C:14]1=2)[CH3:12]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 669599071-Ethyl-3,3,5-trimethyl-7-[(2-pyridin-3-yl-ethylamino)methyl]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Product 1

HCID 50991554N-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-ylmethyl)-N-(2-pyridin-3-ylethyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triethylamine(0.15 ml) was added to a acetonitrile solution (6 ml) of 1-ethyl-3,3,5-trimethyl-7-[(2-pyridin-3-yl-ethylamino)methyl]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione(0.35 g). The mixture was cooled with ice. Benzenesulphonyl chloride(0.13 ml) was added, and the mixture was stirred at room temperature overnight. The reaction liquid was condensed under reduced pressure. Water was added to the residue, followed by extraction by ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by NH silica gel column chromatography (hexane: ethyl acetate=30:70). The purified product was condensed under reduced pressure, and the residue was recrystallized from the ethyl acetate-ether mixture to give the title compound(0.1 g) as a white powder.

Workup

  1. temperatureThe mixture was cooled with ice
  2. customThe reaction liquid
  3. customcondensed under reduced pressure
  4. extractionfollowed by extraction by ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationAfter concentration under reduced pressure
  7. customthe residue was purified by NH silica gel column chromatography (hexane: ethyl acetate=30:70)
  8. customcondensed under reduced pressure
  9. customthe residue was recrystallized from the ethyl acetate-ether mixture

Sources & evidence

ORD record
ord-543ea65674bb4fdc912527028d9cb813
Source dataset
uspto-grants-2015_12
Patent number
US09212187B2

Reaction notes

Loading…