Ethanol → HCID 117987901, compound

HRID 2206121Notes

Reaction equation

HRID 2206121 reaction equation
Br[C:2]1[CH:7]=[N:6][C:5]([O:8][CH3:9])=[C:4]2[N:10]([C:18]3[CH:19]=[C:20]([C:23]([NH2:25])=[O:24])[S:21][CH:22]=3)[N:11]=[C:12]([CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[C:3]=12.C(O)C>[Pd].CN(C=O)C>[CH:13]1([C:12]2[C:3]3[C:4](=[C:5]([O:8][CH3:9])[N:6]=[CH:7][CH:2]=3)[N:10]([C:18]3[CH:19]=[C:20]([C:23]([NH2:25])=[O:24])[S:21][CH:22]=3)[N:11]=2)[CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

5

Reactant 2

HCID 702EthanolHCID 117988001HCID 117988001, compound

Product 1

HCID 117987901HCID 117987901, compoundYield 123%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(4-bromo-3-cyclopentyl-7-methoxy-1H-pyrazolo[3,4-c]pyridin-1-yl)thiophene-2-carboxamide (60 mg) obtained in Step A of Example 67 and 10% palladium/carbon (50% wet, 15 mg) in a mixed solvent of ethanol (10 mL) and DMF (3 mL) was stirred under hydrogen atmosphere at room temperature for 15 hr. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to give the title compound (60 mg).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-917caf6bd96648cd9df921cedfeb180f
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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