Thioglycolic Acid → 1,3,3,5-Tetramethyl-7-[3-(2-pyridin-3-ylethylamino)propoxy]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 1183094Notes

Reaction equation

HRID 1183094 reaction equation
[OH-].[Li+].C(O)(=O)CS.[N+](C1C=CC=CC=1S([N:20]([CH2:42][CH2:43][C:44]1[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=1)[CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:41]=[CH:40][C:28]2[N:29]([CH3:39])[C:30](=[O:38])[C:31]([CH3:37])([CH3:36])[C:32](=[O:35])[N:33]([CH3:34])[C:27]=2[CH:26]=1)(=O)=O)([O-])=O>CN(C=O)C>[CH3:39][N:29]1[C:30](=[O:38])[C:31]([CH3:37])([CH3:36])[C:32](=[O:35])[N:33]([CH3:34])[C:27]2[CH:26]=[C:25]([O:24][CH2:23][CH2:22][CH2:21][NH:20][CH2:42][CH2:43][C:44]3[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=3)[CH:41]=[CH:40][C:28]1=2

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 3939Lithium HydroxideHCID 686742442-nitro-N-(2-pyridin-3-ylethyl)-N-[3-(1,3,3,5-tetramethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yloxy)propyl]benzenesulfonamide

Product 1

HCID 686728731,3,3,5-Tetramethyl-7-[3-(2-pyridin-3-ylethylamino)propoxy]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dioneYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Lithium hydroxide (0.36 g, 15 mmol) and thioglycolic acid (0.48 ml, 6.9 mmol) were added to a DMF solution (20 ml) of 2-nitro-N-(2-pyridin-3-ylethyl)-N-[3-(1,3,3,5-tetramethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yloxy)propyl]benzenesulfonamide (2.05 g, 3.4 mmol), and stirred at room temperature for 3 days. The reaction mixture was added to ice water, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1→dichloromethane:methanol=10:1→4:1). The purified product was concentrated under reduced pressure to thereby obtain 1.13 g (yield: 81%) of 1,3,3,5-tetramethyl-7-[3-(2-pyridin-3-ylethylamino)propoxy]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1→dichloromethane:methanol=10:1→4:1)
  6. concentrationThe purified product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6231c7e931914cc584e598619cc11cdc
Source dataset
uspto-grants-2014_03
Patent number
US08664217B2

Reaction notes

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