(2-Methoxybenzyl)hydrazine → 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

HRID 2196553Notes

Reaction equation

HRID 2196553 reaction equation
[C:1]([C:4]1[C:5]([C:29]([F:32])([F:31])[F:30])=[N:6][N:7]([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[CH2:15][CH2:14]2)[C:8]=1[C:9](OC)=[O:10])(=O)[CH3:2].[CH3:33][O:34][C:35]1[CH:43]=[CH:42][CH:41]=[CH:40][C:36]=1[CH2:37][NH:38][NH2:39]>CCO>[CH3:33][O:34][C:35]1[CH:43]=[CH:42][CH:41]=[CH:40][C:36]=1[CH2:37][N:38]1[C:9](=[O:10])[C:8]2[N:7]([CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[O:20])[CH2:15][CH2:14]3)[N:6]=[C:5]([C:29]([F:31])([F:32])[F:30])[C:4]=2[C:1]([CH3:2])=[N:39]1

Participants

4

Reactant 2

HCID 2760982(2-Methoxybenzyl)hydrazineHCID 59843200benzyl 4-(4-acetyl-5-(methoxycarbonyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Product 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-carboxylateYield 18.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 112 (361 mg, 0.796 mmol) in EtOH (3.2 mL) was added (2-Methoxy-benzyl)-hydrazine (242 mg, 1.592 mmol) and the resulting solution was allowed to stir for 1 h at room temperature, and for 2 h at 75° C. The solvent was evaporated, saturated NaHCO3 was added and the mixture extracted with EtOAc. After the usual work-up the residue was purified via Biotage (10% to 60% EtOAc/Hexane; 12M column) to afford 113 (81 mg. 18.3% yield) as white solid. LRMS (ESI): calc. 555.6; found 556.3 (MH)+.

Workup

  1. waitfor 2 h at 75° C
  2. customThe solvent was evaporated
  3. additionsaturated NaHCO3 was added
  4. extractionthe mixture extracted with EtOAc
  5. customAfter the usual work-up the residue was purified via Biotage (10% to 60% EtOAc/Hexane; 12M column)

Sources & evidence

ORD record
ord-8796d5337cb5479c90904e9f5eff972f
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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