HCID 68294740, compound → HCID 68295355, compound

HRID 1909202Notes

Reaction equation

HRID 1909202 reaction equation
[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([C:28]4[CH2:29][C:30]([CH3:37])([CH3:36])[NH:31][C:32]([CH3:35])([CH3:34])[CH:33]=4)[CH:13]=[C:14]([C:15]([NH:17][CH2:18][C:19]4[C:20](=[O:27])[NH:21][C:22]([CH3:26])=[CH:23][C:24]=4[CH3:25])=[O:16])[C:9]=3[CH:8]=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1>CCO.[Pd]>[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([CH:28]4[CH2:33][C:32]([CH3:35])([CH3:34])[NH:31][C:30]([CH3:37])([CH3:36])[CH2:29]4)[CH:13]=[C:14]([C:15]([NH:17][CH2:18][C:19]4[C:20](=[O:27])[NH:21][C:22]([CH3:26])=[CH:23][C:24]=4[CH3:25])=[O:16])[C:9]=3[CH:8]=[N:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 68294740HCID 68294740, compound

Product 1

HCID 68295355HCID 68295355, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 23938PalladiumSolvent

Procedure

To a stirred solution of 1-cyclopentyl-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(2,2,6,6-tetramethyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (0.06 g, 0.119 mmol) in EtOH (10 mL), 10% Pd/C in catalytic amount was added and stirred it at room temperature under hydrogen pressure (bladder pressure) for 3-5 hr. On completion of reaction, reaction mass filter it through celite bed, then filtrate was concentrated under reduce pressure. The residue was washed with acetonitrile followed by ether to provide the desired product (75% yield). LCMS:505.30 (M+1)+; HPLC: 99.69% (@ 254 nm) (Rt;5.517); 1H NMR (CD3OD-d6, 400 MHz) δ 11.54 (bs, 1H), 8.76 (t, 1H, J=4.8 Hz), 8.26 (s, 1H), 7.51 (s, 1H), 5.89 (s, 1H), 5.38-5.36 (m, 1H), 4.36 (d, 2H, J=4.8 Hz), 2.21 (s, 3H), 2.12 (s, 3H), 2.12 (m, 3H), 2.01-1.98 (m, 2H), 1.96-1.89 (m, 2H), 1.75-1.71 (m, 4H), 1.52 (m, 2H), 1.27 (s, 6H), 1.12 (s, 6H).

Workup

  1. customOn completion of reaction, reaction mass
  2. filtrationfilter it through celite bed
  3. concentrationfiltrate was concentrated
  4. washThe residue was washed with acetonitrile

Sources & evidence

ORD record
ord-2121a59cfcac4781950a9799c5ba1955
Source dataset
uspto-grants-2013_12
Patent number
US08598167B1

Reaction notes

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