HCID 86719568, compound → HCID 70874407, compound

HRID 2208899Notes

Reaction equation

HRID 2208899 reaction equation
[CH2:1]([N:4]([CH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)[C:5]1[C:6]([CH3:25])=[C:7]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[C:8]([NH:10][CH2:11][C:12]1[C:13](=[O:20])[NH:14][C:15]([CH3:19])=[CH:16][C:17]=1[CH3:18])=[O:9])[CH:2]=[CH2:3]>CO.[Pd]>[Cl:24][C:22]1[CH:23]=[C:5]([N:4]([CH2:1][CH2:2][CH3:3])[CH:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[C:6]([CH3:25])=[C:7]([CH:21]=1)[C:8]([NH:10][CH2:11][C:12]1[C:13](=[O:20])[NH:14][C:15]([CH3:19])=[CH:16][C:17]=1[CH3:18])=[O:9]

Participants

4

Reactant 1

HCID 86719568HCID 86719568, compound

Product 1

HCID 70874407HCID 70874407, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 3-(allyl(tetrahydro-2H-pyran-4-yl)amino)-5-chloro-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methylbenzamide (0.10 g) in MeOH (10 mL) was added 10% Pd/C (0.03 g) and the reaction stirred at room temperature under hydrogen (balloon pressure) for 2 h. On completion, the reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure to obtain crude solid which was purified by column chromatography to afford the title compound (0.02 g, 20%). LCMS: 445.25 (M+1)+; HPLC: 90.40% (@ 254 nm) (Rt; 5.609; Method: Column: YMC ODS-A 150 mm×4.6 mm×5μ; Mobile Phase: A; 0.05% TFA in water/B; 0.05% TFA in acetonitrile; Inj. Vol: 10 μL, Col. Temp.: 30° C.; Flow rate: 1.4 mL/min.; Gradient: 5% B to 95% B in 8 min, Hold for 1.5 min, 9.51-12 min 5% B); 1H NMR (DMSO-d6, 400 MHz) δ 11.47 (s, 1H), 8.23 (t, 1H), 7.19 (s, 1H), 6.93 (d, 1H, J=1.6 Hz), 5.88 (s, 1H), 4.24 (d, 2H, J=4.4 Hz), 3.83 (d, 2H, J=10.4 Hz), 3.22-3.25 (m, 2H), 2.94 (t, 2H, J=7.2 Hz), 2.88-2.90 (m, 1H), 2.18 (s, 3H), 2.15 (s, 3H), 2.10 (s, 3H), 1.56 (m, 4H), 1.14-1.23 (m, 2H), 0.75 (t, 3H, J=8 Hz).

Workup

  1. filtrationOn completion, the reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto obtain crude solid which
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-dca4082ae9d540429680b6faadf7a840
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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