7-[3-(4-chloro-2-oxo-3-phenyl-2H-quinoline-1-yl)propoxy]-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione → HCID 70656561, compound

HRID 1504235Notes

Reaction equation

HRID 1504235 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:33]=[CH:32][C:19]3[N:20]([CH2:30][CH3:31])[C:21](=[O:29])[C:22]([CH3:28])([CH3:27])[C:23](=[O:26])[N:24]([CH3:25])[C:18]=3[CH:17]=2)[C:4](=[O:34])[C:3]=1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>[Pd].C(O)C.C(OCC)(=O)C>[CH2:30]([N:20]1[C:21](=[O:29])[C:22]([CH3:28])([CH3:27])[C:23](=[O:26])[N:24]([CH3:25])[C:18]2[CH:17]=[C:16]([O:15][CH2:14][CH2:13][CH2:12][N:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH2:2][CH:3]([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[C:4]3=[O:34])[CH:33]=[CH:32][C:19]1=2)[CH3:31]

Participants

4

Reactant 1

HCID 706565117-[3-(4-chloro-2-oxo-3-phenyl-2H-quinoline-1-yl)propoxy]-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Product 1

HCID 70656561HCID 70656561, compoundYield 55.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

10% Palladium on carbon(20 mg) was added to an ethanol/ethyl acetate solution (1:1, 4 ml) of 7-[3-(4-chloro-2-oxo-3-phenyl-2H-quinoline-1-yl)propoxy]-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione(0.19 g). The mixture was subjected to catalytic reduction at 50° C. under normal pressure for 6 hours. The reaction mixture was subjected to celite filtration to remove the catalyst. The filtrate was condensed under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate=1:1). The purified product was condensed under reduced pressure, and the residue was recrystallized from ether/hexane, thereby obtaining the title compound(0.1 g) as a white powder.

Workup

  1. filtrationThe reaction mixture was subjected to celite filtration
  2. customto remove the catalyst
  3. customcondensed under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane: ethyl acetate=1:1)
  5. customcondensed under reduced pressure
  6. customthe residue was recrystallized from ether/hexane

Sources & evidence

ORD record
ord-8d0cb488da534ee4b6d609ba19f776b6
Source dataset
uspto-grants-2015_12
Patent number
US09212187B2

Reaction notes

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