HCID 18668762, compound → HCID 18668786, compound

HRID 1058629Notes

Reaction equation

HRID 1058629 reaction equation
Cl[C:2]1[C:11]2[N:12]=[C:13]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:14]([CH2:15][CH2:16][CH:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1>[Pd].CO>[C:30]1([C:13]2[N:14]([CH2:15][CH2:16][CH:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)[C:10]3[C:9]4[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=4[N:3]=[CH:2][C:11]=3[N:12]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 1

HCID 18668762HCID 18668762, compound

Product 1

HCID 18668786HCID 18668786, compoundYield 65.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 0.80 g of tert-butyl 4-[2-(4-chloro-2-phenyl-1H-imidazo-[4,5-c]quinolin-1-yl)ethyl]-1-piperidinecarboxylate and 0.30 g of 5% palladium on carbon in 80 ml of methanol was catalytically hydrogenated at ordinary temperature under atmospheric pressure for 12 hours. Mter the reaction, the catalyst was filtered off, and the filtrate was concentrated. The residue was purified by silica gel column chromatography using ethyl acetate—n-heptane (1:1 to 4:1) as eluting solvents and washed with diisopropyl ether to give 0.49 g of pale yellow crystals. Recrystallization from diisopropyl ether gave colorless crystals having the melting point of from 138 to 139° C.

Workup

  1. customMter the reaction
  2. filtrationthe catalyst was filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by silica gel column chromatography
  5. washas eluting solvents
  6. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-2d8ee7dc0af84320adcc70d3892f24df
Source dataset
uspto-grants-2003_02
Patent number
US06518265B1

Reaction notes

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