HCID 59527159, compound → HCID 59527616, compound

HRID 384485Notes

Reaction equation

HRID 384485 reaction equation
C([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]3([OH:34])[CH2:33][CH2:32][CH2:31][CH2:30]3)=[CH:23][CH:22]=2)[C:10]=1[CH3:35])C1C=CC=CC=1>C(O)C.C1COCC1.[Pd]>[OH:34][C:29]1([CH2:28][CH2:27][C:24]2[CH:25]=[CH:26][C:21]([O:20][CH2:19][C:11]3[NH:12][C:13]4[C:18]([C:9](=[O:8])[C:10]=3[CH3:35])=[CH:17][CH:16]=[CH:15][CH:14]=4)=[CH:22][CH:23]=2)[CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

4

Reactant 1

HCID 59527159HCID 59527159, compound

Product 1

HCID 59527616HCID 59527616, compoundYield 49.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of 1-[2-(4-{[4-(benzyloxy)-3-methylquinolin-2-yl]methoxy}phenyl)ethyl]cyclopentanol (128 mg) in ethanol-THF (1:1, 4 mL) was added 10% palladium-activated carbon (30 mg) under nitrogen atmosphere, followed by stirring at room temperature under hydrogen atmosphere for 3 hours. The catalyst was removed by filtration, and then the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol=92/8). The resulting solid was washed with ether and dried to obtain 2-({4-[2-(1-hydroxycyclopentyl)ethyl]phenoxy}methyl)-3-methylquinolin-4(1H)-one (51 mg) as a crystal.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol=92/8)
  4. washThe resulting solid was washed with ether
  5. customdried

Sources & evidence

ORD record
ord-82c4756300924f24ae7903617e2bd49a
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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