HCID 86723767, compound → HCID 86723768, compound

HRID 577538Notes

Reaction equation

HRID 577538 reaction equation
C([O:8][C:9]1[C:14]([CH2:15][N:16]2[CH2:25][CH2:24][C:23]3[C:18](=[C:19]([CH3:36])[C:20]([O:32][CH:33]([CH3:35])[CH3:34])=[CH:21][C:22]=3[C:26]3[CH:27]=[N:28][N:29]([CH3:31])[CH:30]=3)[C:17]2=[O:37])=[C:13]([CH3:38])[CH:12]=[C:11]([CH3:39])[N:10]=1)C1C=CC=CC=1>CO.[Pd]>[CH3:38][C:13]1[CH:12]=[C:11]([CH3:39])[NH:10][C:9](=[O:8])[C:14]=1[CH2:15][N:16]1[CH2:25][CH2:24][C:23]2[C:18](=[C:19]([CH3:36])[C:20]([O:32][CH:33]([CH3:34])[CH3:35])=[CH:21][C:22]=2[C:26]2[CH:27]=[N:28][N:29]([CH3:31])[CH:30]=2)[C:17]1=[O:37]

Participants

4

Reactant 1

HCID 86723767HCID 86723767, compound

Product 1

HCID 86723768HCID 86723768, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-methyl-5-(1-methyl-1H-pyrazol-4-yl)-7-(propan-2-yloxy)-3,4-dihydroisoquinolin-1(2H)-one (108k, 40 mg, 0.076 mmol) and 10% Pd/C (20 mg) in MeOH (10 mL) was hydrogenated under an H2 balloon at room temperature for 16 hours. The reaction mixture was filtered and the filtrate was concentrated under vacuum. The residue was purified by prep. TLC (EtOAc) to give the title compound (Example 108, 19 mg, 58%) as a white solid. 1H NMR (400 MHz, methanol-d4) δ 7.72 (s, 1H), 7.56 (s, 1H), 7.03 (s, 1H), 6.11 (s, 1H), 4.78 (s, 3H), 4.6-4.57 (m, 1H), 3.92 (s, 3H), 3.92 (s, 3H), 2.82-2.81 (m, 2H), 2.47 (s, 3H), 2.28-2.24 (m, 5H), 1.34-1.32 (d, 6H); MS 435.2 [M+H].

Workup

  1. customat room temperature
  2. customfor 16 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under vacuum
  5. customThe residue was purified by prep

Sources & evidence

ORD record
ord-7cae432460be491ba85fc11a51d9c046
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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