HCID 70656511, compound → HCID 70656561, compound

HRID 69063Notes

Reaction equation

HRID 69063 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 70656511HCID 70656511, compound

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-706f8db54db54089885c0b405b3b4e82
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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