Tetrahydrofuran → HCID 178458932, compound

HRID 2282196Notes

Reaction equation

HRID 2282196 reaction equation
[CH3:1][C:2]1[C:10]([C:11]2[S:12][C:13]([C:20]3[NH:24][CH:23]=[N:22][N:21]=3)=[C:14]([O:16][CH2:17][CH:18]=[CH2:19])[N:15]=2)=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.O1CCCC1>C(O)C.[Pd]>[CH3:1][C:2]1[C:10]([C:11]2[S:12][C:13]([C:20]3[NH:24][CH:23]=[N:22][N:21]=3)=[C:14]([O:16][CH2:17][CH2:18][CH3:19])[N:15]=2)=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 178458931HCID 178458931, compound

Product 1

HCID 178458932HCID 178458932, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-methyl-3-[4-(prop-2-en-1-yloxy)-5-(4H-1,2,4-triazol-3-yl)-1,3-thiazol-2-yl]pyrazolo[1,5-a]pyridine (70 mg, 0.55 mmol) produced in Example 27 in ethanol (15 mL)-tetrahydrofuran (15 mL) was added 10% palladium/carbon (73 mg), and the mixture was stirred at room temperature for 5 hr under a hydrogen atmosphere (1 atm). Palladium/carbon was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was washed with diisopropyl ether to give the title compound (43 mg, 61%) as a yellow solid.

Workup

  1. filtrationPalladium/carbon was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washThe obtained residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-fd2af53906be4fe082e8717dee2f6a41
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

Loading…