HCID 66855656, compound → HCID 66854700, compound

HRID 1530107Notes

Reaction equation

HRID 1530107 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([C:17]4[S:18][C:19]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:20]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[N:21]=4)=[C:14]([CH3:16])[N:15]=3)[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1>C(O)(=O)C.CO.[C].[Pd]>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([C:17]4[S:18][C:19]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:20]([C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=5)[N:21]=4)=[C:14]([CH3:16])[N:15]=3)[CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 1

HCID 66855656HCID 66855656, compound

Product 1

HCID 66854700HCID 66854700, compoundYield 76.8%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a mixture of ethyl 2-(6-cyclohex-1-en-1-yl-2-methylimidazo[1,2-a]pyridin-3-yl)-4-phenyl-1,3-thiazole-5-carboxylate (200 mg, 0.45 mmol) obtained above in acetic acid (18 mL) and MeOH (18 mL), was added 10% palladium-carbon (100 mg), and the mixture was stirred at rt for 15 h under a hydrogen atmosphere (1 atm). Insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure. To the residue was added saturated aqueous solution of sodium bicarbonate (10 mL) and water (10 mL), and the resulting precipitate was collected by filtration, which was washed with diethyl ether to give the title compound (154 mg, 69%) as a black solid.

Workup

  1. customInsoluble materials were removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the residue was added saturated aqueous solution of sodium bicarbonate (10 mL) and water (10 mL)
  4. filtrationthe resulting precipitate was collected by filtration, which
  5. washwas washed with diethyl ether

Sources & evidence

ORD record
ord-0609313190dc44c79ae396967332bf07
Source dataset
uspto-grants-2015_07
Patent number
US09090601B2

Reaction notes

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