HCID 70874784, compound → HCID 70874982, compound

HRID 2208717Notes

Reaction equation

HRID 2208717 reaction equation
[CH:1]1([N:6]([CH3:34])[C:7]2[C:8]([CH3:33])=[C:9]([CH:23]=[C:24]([C:26]3[CH2:27][CH2:28][N:29]([CH3:32])[CH2:30][CH:31]=3)[CH:25]=2)[C:10]([NH:12][CH2:13][C:14]2[C:15](=[O:22])[NH:16][C:17]([CH3:21])=[CH:18][C:19]=2[CH3:20])=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C.[Pd]>[CH:1]1([N:6]([CH3:34])[C:7]2[C:8]([CH3:33])=[C:9]([CH:23]=[C:24]([CH:26]3[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]3)[CH:25]=2)[C:10]([NH:12][CH2:13][C:14]2[C:15](=[O:22])[NH:16][C:17]([CH3:21])=[CH:18][C:19]=2[CH3:20])=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 70874784HCID 70874784, compound

Product 1

HCID 70874982HCID 70874982, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-(cyclopentyl(methyl)amino)-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methyl-5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)benzamide (0.045 g, 0.097 mmol) in ethanol added 10% Pd/C and the reaction was stirred under H2 at bladder pressure. After complete consumption of the starting material reaction mixture was filtered through celite. The filtrate was concentrated and triturated in acetonitrile and filtered to provide the desired compound (0.030 g, 66%): LCMS: 465.40 (M+1)+; HPLC: 95.39% (@ 254 nm) (Rt; 3.884; 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 11.44 (s, 1H), 7.98 (t, 1H), 7.00 (s, 1H), 6.77 (s, 1H), 5.85 (s, 1H), 4.25 (d, 2H, J=4.4 Hz), 3.42 (m, 1H), 2.84 (d, 2H, J=11.2 Hz), 2.47 (s, 3H), 2.37 (m, 1H), 2.18 (s, 6H), 2.15 (s, 3H), 2.10 (s, 3H), 1.93 (t, 2H, J=10.8 Hz), 1.70-1.55 (m, 8H), 1.48 (m, 2H), 1.38 (m, 2H).

Workup

  1. customAfter complete consumption of the starting material reaction mixture
  2. filtrationwas filtered through celite
  3. concentrationThe filtrate was concentrated
  4. customtriturated in acetonitrile
  5. filtrationfiltered

Sources & evidence

ORD record
ord-3aa02f1cbe4144748091e2d326bafd63
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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