Water → 7-{[N-(1-Benzyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-ylmethyl)-N-methylamino]methyl}-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 68977Notes

Reaction equation

HRID 68977 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][NH:19][CH2:20][C:21]3[CH:38]=[CH:37][C:24]4[N:25]([CH2:35][CH3:36])[C:26](=[O:34])[C:27]([CH3:33])([CH3:32])[C:28](=[O:31])[N:29]([CH3:30])[C:23]=4[CH:22]=3)[CH:16]=2)[CH2:11][CH2:10][C:9]1=[O:39])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:42]I.O>CN(C=O)C>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][N:19]([CH2:20][C:21]3[CH:38]=[CH:37][C:24]4[N:25]([CH2:35][CH3:36])[C:26](=[O:34])[C:27]([CH3:33])([CH3:32])[C:28](=[O:31])[N:29]([CH3:30])[C:23]=4[CH:22]=3)[CH3:42])[CH:16]=2)[CH2:11][CH2:10][C:9]1=[O:39])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 706571187-{[N-(1-Benzyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-ylmethyl) amino]methyl}-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Product 1

HCID 706575117-{[N-(1-Benzyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-ylmethyl)-N-methylamino]methyl}-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dioneYield 66.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

7-{[N-(1-Benzyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-ylmethyl) amino]methyl}-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (247 mg) was dissolved in DMF (2 ml), and was cooled to 0° C. in ice water bath. Sodium hydride (60% in oil, 13.56 mg) was added thereto at the same temperature, and the mixture was stirred at 0° C. for 0.5 hours. Methyl iodide (73.5 mg) was added thereto, and the mixture was stirred at room temperature for 4 hours. Water was added to the reaction mixture, followed by extraction using ethyl acetate. The organic layer was dried with sodium sulfate, and was condensed under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane:methanol=10:1). The purified product was condensed to dryness under reduced pressure to give the title compound (169 mg) as a white amorphous.

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hours
  2. extractionfollowed by extraction
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. customcondensed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=10:1)
  6. customcondensed to dryness under reduced pressure

Sources & evidence

ORD record
ord-0746928562ef4a01bee8ab51954f91f1
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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