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 68965Notes

Reaction equation

HRID 68965 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.

Workup

  1. temperatureThe mixture was cooled with ice
  2. customThe reaction liquid
  3. customcondensed under reduced pressure
  4. extractionfollowed by extraction by ethyl acetate

Sources & evidence

ORD record
ord-df3bb7aee26f46838cb1ff75b2a25850
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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