HCID 68154117, compound → HCID 67111534, compound

HRID 341085Notes

Reaction equation

HRID 341085 reaction equation
[O:1]=[C:2]1[C:6]2=[CH:7][N:8]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[CH:25][CH:24]=[N:23]4)=[CH:18][CH:17]=3)[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:5]2=[N:4][N:3]1[CH:27]1[CH2:32][CH2:31][N:30](C(OCC2C=CC=CC=2)=O)[CH2:29][CH2:28]1>C(OCC)(=O)C.[OH-].[Pd+2].[OH-]>[NH:30]1[CH2:31][CH2:32][CH:27]([N:3]2[C:2](=[O:1])[C:6]3=[CH:7][N:8]([CH2:15][C:16]4[CH:21]=[CH:20][C:19]([N:22]5[CH:26]=[CH:25][CH:24]=[N:23]5)=[CH:18][CH:17]=4)[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=4[C:5]3=[N:4]2)[CH2:28][CH2:29]1

Participants

4

Reactant 1

HCID 68154117HCID 68154117, compound

Product 1

HCID 67111534HCID 67111534, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Phenylmethyl 4-(3-oxo-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-3,5-dihydro-2H-pyrazolo[4,3-c]quinolin-2-yl)piperidine-1-carboxylate (Example 511, 25 mg, 0.045 mmol) was dissolved in ethyl acetate, treated with palladium(II) hydroxide on carbon (2.5 mg, 0.1 wt equiv), sparged under an atmosphere of hydrogen (1 atm) and stirred for 1 hour at ambient temperature. The mixture was sparged under an atmosphere of nitrogen, filtered through a pad of Celite and the filtrate was concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 80:20; dichloromethane:methanol), providing the titled compound: 1H-NMR (400 MHz, CDCl3) δ 8.83 (1H, s), 8.38-8.36 (1H, m), 7.89 (1H, d, J=2.4 Hz), 7.71 (1H, d, J=1.8 Hz), 7.69 (2H, d, j=8.7 Hz), 7.52-7.43 (3H, m), 7.30-7.26 (3H, m), 6.46 (1H, m), 5.59 (2H, s), 4.61 (1H, m), 3.58-3.50 (2H, m), 3.01-2.96 (2H, m), 2.65-2.57 (2H, m), 2.13-2.05 (2H, m) ppm; low resolution mass spectrometry (ES+) m/z 424.9 [(M+H)+; calculated for C25H25N6O: 425.2].

Workup

  1. customsparged under an atmosphere of hydrogen (1 atm)
  2. customThe mixture was sparged under an atmosphere of nitrogen
  3. filtrationfiltered through a pad of Celite
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by silica gel gradient chromatography (100:0 to 80:20; dichloromethane:methanol)

Sources & evidence

ORD record
ord-42431769157b4d388c228c9b00ca98c5
Source dataset
uspto-grants-2014_11
Patent number
US08895580B2

Reaction notes

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