benzyl 4-(6-(2-methoxybenzyl)-4-methyl-7-oxo-3-(trifluoromethyl)-6,7-dihydro-1H-pyrazolo[3,4-d]pyridazin-1-yl)piperidine-1-carboxylate → 6-(2-methoxybenzyl)-4-methyl-1-(piperidin-4-yl)-3-(trifluoromethyl)-1H-pyrazolo[3,4-d]pyridazin-7(6H)-one

HRID 2196554Notes

Reaction equation

HRID 2196554 reaction equation
[CH3:1][O:2][C:3]1[CH:40]=[CH:39][CH:38]=[CH:37][C:4]=1[CH2:5][N:6]1[C:11](=[O:12])[C:10]2[N:13]([CH:20]3[CH2:25][CH2:24][N:23](C(OCC4C=CC=CC=4)=O)[CH2:22][CH2:21]3)[N:14]=[C:15]([C:16]([F:19])([F:18])[F:17])[C:9]=2[C:8]([CH3:36])=[N:7]1>CCO.[Pd]>[CH3:1][O:2][C:3]1[CH:40]=[CH:39][CH:38]=[CH:37][C:4]=1[CH2:5][N:6]1[C:11](=[O:12])[C:10]2[N:13]([CH:20]3[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]3)[N:14]=[C:15]([C:16]([F:17])([F:18])[F:19])[C:9]=2[C:8]([CH3:36])=[N:7]1

Participants

4

Reactant 1

HCID 59843219benzyl 4-(6-(2-methoxybenzyl)-4-methyl-7-oxo-3-(trifluoromethyl)-6,7-dihydro-1H-pyrazolo[3,4-d]pyridazin-1-yl)piperidine-1-carboxylate

Product 1

HCID 598433326-(2-methoxybenzyl)-4-methyl-1-(piperidin-4-yl)-3-(trifluoromethyl)-1H-pyrazolo[3,4-d]pyridazin-7(6H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 113 (81 mg, 0.146 mmol) in EtOH (1.5 mL) was added Pd/C (10% Degussa type, 15.5 mg, 0.015 mmol). The resulting suspension was allowed to stir for 30 min at room temperature under latm of H2 gas. The catalyst was filtrate over Celite and the solvent was evaporated to give crude 114. LRMS (ESI): calc. 421.4; found 422.3 (MH)+.

Workup

  1. customthe solvent was evaporated
  2. customto give crude 114

Sources & evidence

ORD record
ord-1a71e0041bbc4ccfa3e727595ca54f4c
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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