HCID 59560619, compound → HCID 59560608, compound

HRID 1518008Notes

Reaction equation

HRID 1518008 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][C:14]2=[N:17][N:18]([C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([O:30][CH3:31])[CH:28]=4)[N:23]=[CH:22][CH:21]=3)[CH:19]=[C:13]2[CH2:12]1)=O)C1C=CC=CC=1>CCO.[Pd]>[CH3:31][O:30][C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][CH:26]=1)[N:23]=[CH:22][CH:21]=[C:20]2[N:18]1[CH:19]=[C:13]2[CH2:12][NH:11][CH2:16][CH2:15][C:14]2=[N:17]1

Participants

4

Reactant 1

HCID 59560619HCID 59560619, compound

Product 1

HCID 59560608HCID 59560608, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-(6-methoxy-quinolin-4-yl)-2,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid benzyl ester (300 mg, 0.7 mmol) in EtOH (3 mL) was added HCO2NH4 (70 mg, 1 mmol) and 10% Pd/C (300 mg). The mixture was stirred at RT for 16 h. The crude mixture was filtered through diatomaceous earth, washing with EtOH (10 mL), and the filtrate was concentrated to afford 203 mg (100% crude) of the title compound as a pale yellow foam. MS (ESI): exact mass calculated for C16H16N4O, 280.13; m/z found, 281.32 [M+H]+. 1H NMR (3:2 mixture of isomers; 500 MHz, CDCl3): 8.80-8.79 (m, 0.6H), 8.78-8.76 (m, 0.4H), 8.08-8.05 (m, 1H), 7.73-7.62 (m, 2H), 7.24-7.18 (m, 0.6H), 7.11 (s, 0.4H), 5.00 (s, 2H), 4.68 (s, 0.8H), 4.52 (s, 1.2H), 3.61-3.58 (m, 3H), 3.01 (td, J=6.9, 3.3, 0.6H), 2.54 (s, 0.4H), 2.38 (s, 1H), 2.02 (t, J=7.9, 1H).

Workup

  1. filtrationThe crude mixture was filtered through diatomaceous earth
  2. washwashing with EtOH (10 mL)
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-fa41773bceac40ccaf1623029a51b7c1
Source dataset
uspto-grants-2012_07
Patent number
US08232391B2

Reaction notes

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