[2-(6-Methoxy-indazol-1-yl)-1-methyl-ethyl]-carbamic Acid Benzyl Ester → 1-(6-methoxy-1H-indazol-1-yl)propan-2-amine

HRID 967714Notes

Reaction equation

HRID 967714 reaction equation
C(OC(=O)[NH:10][CH:11]([CH3:24])[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH3:23])[CH:20]=2)[CH:15]=[N:14]1)C1C=CC=CC=1>CO.[Pd]>[CH3:23][O:22][C:19]1[CH:20]=[C:21]2[C:16]([CH:15]=[N:14][N:13]2[CH2:12][CH:11]([NH2:10])[CH3:24])=[CH:17][CH:18]=1

Participants

4

Reactant 1

HCID 69752536[2-(6-Methoxy-indazol-1-yl)-1-methyl-ethyl]-carbamic Acid Benzyl Ester

Product 1

HCID 697543251-(6-methoxy-1H-indazol-1-yl)propan-2-amineYield 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of the product from Step B (0.68 g, 2.0 mmol) in methanol was added Pd/C (10%, 0.10 g) under a nitrogen atmosphere at room temperature. The mixture was stirred for 20 h under a hydrogen atmosphere and filtered through a filter aid. The filtrate was evaporated to a residue which was purified by chromatography (silica, 5% methanol in dichloromethane to 10% methanol in dichloromethane) to give a syrup (0.40 g, 97%). Treatment of the syrup with fumaric acid gave a residue that was recrystallized from methanol/ether to provide a colorless solid: mp 151–152° C.; MS (ES) m/z 206 (M+). Analysis. Calculated for C11H15N3O.1.0 C4H4O4. 1.0H2O: C, 53.09; H, 6.24; N, 12.38. Found: C, 52.88; H, 6.31; N, 12.14.

Workup

  1. filtrationfiltered through a filter aid
  2. customThe filtrate was evaporated to a residue which
  3. customwas purified by chromatography (silica, 5% methanol in dichloromethane to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-07e5dd41fbdd48e0854c1d3773b4ea3e
Source dataset
uspto-grants-2005_10
Patent number
US06956036B1

Reaction notes

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