Acetic Acid → HCID 22933846, compound

HRID 1269895Notes

Reaction equation

HRID 1269895 reaction equation
[CH3:1][C:2]([CH3:4])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[NH2:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][N:28]=[CH:27]2>ClCCCl>[CH:2]([NH:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][N:28]=[CH:27]2)([CH3:4])[CH3:1]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 880121H-Indazol-5-amineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 22933846HCID 22933846, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Acetone (25 μl, 0.340 mmol), sodium triacetoxyborohydride (83 mg, 0.392 mmol) and acetic acid (18 μl, 0.314 mmol) were added in that order to a solution of 5-amino-1H-indazole (40 mg, 0.300 mmol) in 1,2-dichloroethane (1 ml), and the resulting mixture was stirred at room temperature for 20 hours. The reaction was terminated by the use of a saturated aqueous sodium hydrogencarbonate solution (4 ml), followed by extraction with ethyl acetate. The solvent was distilled off under reduced pressure to obtain a crude product. The crude product was purified by a silica gel column chromatography (eluent: chloroform/methanol=100/2) to obtain N-isopropyl-1H-indazol-5-amine (40 mg, 76%).

Workup

  1. customThe reaction was terminated by the use of a saturated aqueous sodium hydrogencarbonate solution (4 ml)
  2. extractionfollowed by extraction with ethyl acetate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customto obtain a crude product
  5. customThe crude product was purified by a silica gel column chromatography (eluent: chloroform/methanol=100/2)

Sources & evidence

ORD record
ord-bd22b7d05d5c43878b3e0c6b128986c0
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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