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

HRID 2196081Notes

Reaction equation

HRID 2196081 reaction equation
C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[N+:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([NH:24][CH2:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)(=[O:23])=[O:22])([O-:14])=[O:13].[CH2:33]([N:35]1[C:41](=[O:42])[C:40]([CH3:44])([CH3:43])[C:39](=[O:45])[N:38]([CH3:46])[C:37]2[CH:47]=[C:48]([O:51][CH2:52][CH2:53][CH2:54]I)[CH:49]=[CH:50][C:36]1=2)[CH3:34]>C(OCC)(=O)C.O>[N+:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([N:24]([CH2:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)[CH2:54][CH2:53][CH2:52][O:51][C:48]1[CH:49]=[CH:50][C:36]2[N:35]([CH2:33][CH3:34])[C:41](=[O:42])[C:40]([CH3:44])([CH3:43])[C:39](=[O:45])[N:38]([CH3:46])[C:37]=2[CH:47]=1)(=[O:22])=[O:23])([O-:14])=[O:13]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 465565342-nitro-N-(2-pyridin-3-ylethyl)benzenesulfonamideHCID 686727921-Ethyl-7-(3-iodopropoxy)-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Product 1

HCID 686735912-nitro-N-(2-pyridin-3-ylethyl)-N-[3-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yloxy)propyl]benzenesulfonamideYield 107.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (1.89 g, 13.7 mmol) was added to a DMF solution (50 ml) of 2-nitro-N-(2-pyridin-3-ylethyl)benzene sulfonamide (1.40 g, 4.56 mmol) and 1-ethyl-7-(3-iodopropoxy)-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (2.16 g, 5.0 mmol), and stirred at room temperature overnight. Water was added to the reaction mixture, and extraction with ethyl acetate was performed. The organic layer was washed with water and a saturated sodium chloride aqueous solution in this order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=1:0→10:1). The purified product was concentrated under reduced pressure to thereby obtain 2.99 g (yield: quantitative) of 2-nitro-N-(2-pyridin-3-ylethyl)-N-[3-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yloxy)propyl]benzenesulfonamide as a yellow oil.

Workup

  1. washThe organic layer was washed with water
  2. dry with materiala saturated sodium chloride aqueous solution in this order, dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=1:0→10:1)
  5. concentrationThe purified product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c31c85d49f8e4d6bb1751ac65fd1008d
Source dataset
uspto-grants-2012_12
Patent number
US08338406B2

Reaction notes

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