Sodium borohydride → 7-{[N-(1-Benzyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-ylmethyl)amino]methyl}-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 68976Notes

Reaction equation

HRID 68976 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([CH:18]=O)=[CH:15][CH:16]=2)[CH2:11][CH2:10][C:9]1=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:21][CH2:22][C:23]1[CH:40]=[CH:39][C:26]2[N:27]([CH2:37][CH3:38])[C:28](=[O:36])[C:29]([CH3:35])([CH3:34])[C:30](=[O:33])[N:31]([CH3:32])[C:25]=2[CH:24]=1.[BH4-].[Na+]>CO>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([CH2:18][NH:21][CH2:22][C:23]3[CH:40]=[CH:39][C:26]4[N:27]([CH2:37][CH3:38])[C:28](=[O:36])[C:29]([CH3:35])([CH3:34])[C:30](=[O:33])[N:31]([CH3:32])[C:25]=4[CH:24]=3)=[CH:15][CH:16]=2)[CH2:11][CH2:10][C:9]1=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 706570611-Ethyl-3,3,5-trimethyl-7-aminomethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dioneHCID 888769381-Benzyl-2-oxo-3,4-dihydroquinoline-6-carbaldehyde

Product 1

HCID 706570677-{[N-(1-Benzyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-ylmethyl)amino]methyl}-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dioneYield 98.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Benzyl-2-oxo-1,2,3,4-tetrahydroquinoline-6-carbaldehyde (0.205 g) was added to a methanol solution (10 ml) of 7-(aminomethyl)-1-ethyl-3,3,5-trimethyl-1H-benzo[b][1,4]diazepine-2,4(3H, 5H)-dione (0.213 g). The mixture was stirred at room temperature overnight. Sodium borohydride (0.022 g) was added to the mixture, and the mixture was stirred at room temperature overnight. The liquid was then condensed under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:methanol=9:1). The purified product was condensed under reduced pressure to give the title compound (0.400 g) as a white amorphous. 1H NMR (CDCl3), δppm: 0.82 (3H, s), 1.17 (3H, t, J=7.1 Hz), 1.53 (3H, s), 2.77-2.81 (2H, m), 2.96-3.00 (2H, m), 3.40 (3H, s), 3.73 (2H, s), 3.74-3.83 (1H, m), 3.81 (2H, s), 4.12-4.17 (1H, m), 5.17 (2H, s), 6.83 (1H, d, J=8.3 Hz), 7.05 (1H, dd, J=1.9, 8.3 Hz), 7.16 (1H, d, J=1.6 Hz), 7.19-7.25 (6H, m), 7.27-7.33 (2H, m)

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customcondensed under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate:methanol=9:1)
  4. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-e19add80fa1d4fb08bc2241c337aa7e7
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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