HCID 86665108, compound → HCID 66980661, compound

HRID 1038838Notes

Reaction equation

HRID 1038838 reaction equation
C1(C(C2C=CC=CC=2)=[N:8][C:9]2[CH:17]=[C:16]3[C:12]([CH:13]=[N:14][N:15]3[CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][O:19]3)=[C:11]([CH3:24])[CH:10]=2)C=CC=CC=1>CO.[Pd]>[CH3:24][C:11]1[CH:10]=[C:9]([NH2:8])[CH:17]=[C:16]2[C:12]=1[CH:13]=[N:14][N:15]2[CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1

Participants

4

Reactant 1

HCID 86665108HCID 86665108, compound

Product 1

HCID 66980661HCID 66980661, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-(diphenylmethylene)-4-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-amine (0.80 g, 2.0 mmol, prepared using B from Preparation #AB.1 with diphenylmethanimine [Alfa Aesar]) and Pd/C (0.080 g, 0.752 mmol, 10 wt %) in MeOH (10 mL) were stirred at rt for about 16 h under a H2 atmosphere. The mixture was filtered through Celite® and the filter cake was washed with MeOH. The filtrate was concentrated to provide 4-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-amine (0.45 g, 74%): LC/MS (Table 2, Method h) Rt=1.76 min; MS m/z: 232 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. washthe filter cake was washed with MeOH
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-364594fe9f644866b8b8f6281ae31626
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

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