Ethylacetate methanol → HCID 86723755, compound

HRID 577527Notes

Reaction equation

HRID 577527 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]([CH3:30])[C:20]([O:26][CH:27]([CH3:29])[CH3:28])=[CH:21][CH:22]=3)[C:17]2=[O:31])=[C:13]([CH3:32])[CH:12]=[C:11]([CH3:33])[N:10]=1)C1C=CC=CC=1.CCOC(C)=O.CO>[Pd].CO>[CH3:32][C:13]1[CH:12]=[C:11]([CH3:33])[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]([CH3:30])[C:20]([O:26][CH:27]([CH3:28])[CH3:29])=[CH:21][CH:22]=2)[C:17]1=[O:31]

Participants

5

Reactant 2

HCID 21584119Ethylacetate methanolHCID 86723753HCID 86723753, compound

Product 1

HCID 86723755HCID 86723755, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-methyl-7-(propan-2-yloxy)-3,4-dihydroisoquinolin-1(2H)-one (107b, 46 mg, 0.10 mmol) and 10% palladium on carbon (10 mg) in methanol (3 mL) was hydrogenated at 1 atmosphere using a balloon for 26 hours. The reaction mixture was filtered through CELITE® then the filtrate was concentrated under vacuum. The residue was purified by column chromatography (EtOAc/heptanes, 50/50-100/0 then EtOAc/MeOH, 100/0-70/30), to give the title compound (Example 107, 27 mg, 74% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 11.52 (br. s., 1H), 7.05-7.01 (m, 1H), 6.99 (s, 1H), 5.87 (s, 1H), 4.58 (s, 2H), 4.51 (td, J=5.9, 12.1 Hz, 1H), 2.68 (t, J=6.0 Hz, 2H), 2.42 (s, 3H), 2.13 (s, 3H), 2.11 (s, 2H), 1.25 (d, J=5.9 Hz, 6H); MS 355 (M+H).

Workup

  1. customfor 26 hours
  2. filtrationThe reaction mixture was filtered through CELITE®
  3. concentrationthe filtrate was concentrated under vacuum
  4. customThe residue was purified by column chromatography (EtOAc/heptanes, 50/50-100/0

Sources & evidence

ORD record
ord-ceffa5cc7bfc49088dfff515a25b5bfa
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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