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 1504150Notes

Reaction equation

HRID 1504150 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-c285e07c712f444ea3b01a688b604c09
Source dataset
uspto-grants-2015_12
Patent number
US09212187B2

Reaction notes

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