HCID 86723741, compound → HCID 86723742, compound

HRID 577515Notes

Reaction equation

HRID 577515 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]([CH3:31])[C:20]([C:26]([N:28]([CH3:30])[CH3:29])=[O:27])=[CH:21][CH:22]=3)[C:17]2=[O:32])=[C:13]([CH3:33])[CH:12]=[C:11]([CH3:34])[N:10]=1)C1C=CC=CC=1>CO.[Pd]>[CH3:33][C:13]1[CH:12]=[C:11]([CH3:34])[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]([CH3:31])[C:20]([C:26]([N:28]([CH3:29])[CH3:30])=[O:27])=[CH:21][CH:22]=2)[C:17]1=[O:32]

Participants

4

Reactant 1

HCID 86723741HCID 86723741, compound

Product 1

HCID 86723742HCID 86723742, compoundYield 49.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-N,N,8-trimethyl-1-oxo-1,2,3,4-tetrahydroisoquinoline-7-carboxamide (76f, 80 mg, 0.175 mmol) and 10% Pd/C (10 mg) in MeOH (10 mL) was hydrogenated under H2 balloon at room temperature for 20 hours. The mixture was filtered and the solids were washed with MeOH (2×10 mL). The filtrate was concentrated under vacuum and the residue was purified by column chromatography (EtOAc/MeOH=5:1) to give the title compound (Example 76, 32 mg, 49.7%) as a white solid. 1H NMR (400 MHz, methanol-d4) δ 7.22-7.2 (d, 1H), 7.17-7.15 (d, 1H), 6.11 (s, 1H), 4.77 (s, 2H), 3.45-3.43 (m, 2H), 3.13 (s, 3H), 2.9-2.85 (m, 5H), 2.28 (s, 3H), 2.25 (s, 3H); MS 367.9 [M+H].

Workup

  1. customat room temperature
  2. customfor 20 hours
  3. filtrationThe mixture was filtered
  4. washthe solids were washed with MeOH (2×10 mL)
  5. concentrationThe filtrate was concentrated under vacuum
  6. customthe residue was purified by column chromatography (EtOAc/MeOH=5:1)

Sources & evidence

ORD record
ord-ed066347f3994f6d8d88b3a4cada29e0
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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