HCID 86723765, compound → HCID 86723766, compound

HRID 577536Notes

Reaction equation

HRID 577536 reaction equation
[CH3:1][C:2]1[C:3]([O:19][CH:20]([CH3:22])[CH3:21])=[CH:4][C:5]([C:13]2[CH:14]=[N:15][N:16]([CH3:18])[CH:17]=2)=[C:6]2[C:11]=1[C:10](=[O:12])[NH:9][CH:8]=[CH:7]2>CCO.[Pd]>[CH3:1][C:2]1[C:3]([O:19][CH:20]([CH3:22])[CH3:21])=[CH:4][C:5]([C:13]2[CH:14]=[N:15][N:16]([CH3:18])[CH:17]=2)=[C:6]2[C:11]=1[C:10](=[O:12])[NH:9][CH2:8][CH2:7]2

Participants

4

Reactant 1

HCID 86723765HCID 86723765, compound

Product 1

HCID 86723766HCID 86723766, compoundYield 78.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 8-methyl-5-(1-methyl-1H-pyrazol-4-yl)-7-(propan-2-yloxy)isoquinolin-1(2H)-one (108i, 0.14 g, 0.47 mmol) and 10% Pd/C (0.3 g) in EtOH (20 mL) was hydrogenated under H2 (1.6 MPa) at 80° C. for 48 hours in a 50 mL autoclave. The reaction mixture was filtered and the solids were washed with EtOH (2×10 mL). The filtrate was concentrated under vacuum to give 8-methyl-5-(1-methyl-1H-pyrazol-4-yl)-7-(propan-2-yloxy)-3,4-dihydroisoquinolin-1(2H)-one (108j, 0.11 g, 78.7%) as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solids were washed with EtOH (2×10 mL)
  3. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-102d5b804b1642309249aea26e8882e1
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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