Methanol → HCID 17838053, compound

HRID 1352174Notes

Reaction equation

HRID 1352174 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[NH2:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][N:14]=[CH:13]2.CO.[BH4-].[Na+]>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].C(OCC)(=O)C.O>[NH:15]1[C:16]2[C:12](=[CH:11][C:10]([NH:9][CH:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[CH:18][CH:17]=2)[CH:13]=[N:14]1

Participants

8

Reactant 4

HCID 887MethanolHCID 740491-Methyl-4-piperidoneHCID 880121H-Indazol-5-amineHCID 4311764Sodium borohydride

Product 1

HCID 17838053HCID 17838053, compoundYield 41.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 11026Titanium isopropoxideSolvent

Procedure

1-Methyl-4-piperidone (300 mg) was dissolved in titanium tetraisopropoxide (1.5 g). 5-Aminoindazole (282 mg) was added to the solution, and the mixture was stirred at room temperature for 18 hr. Methanol and sodium borohydride (50 mg) were added to the reaction solution, and the mixture was stirred for 18 hr. The reaction solution was diluted with ethyl acetate, and a minor amount of water was added thereto, and the mixture was then filtered under the reduced pressure. The filtrate was concentrated under the reduced pressure, and the residue was purified by column chromatography on silica gel [chloroform/methanol] to give the title compound (202 mg, yield 41.4%).

Workup

  1. stirringthe mixture was stirred for 18 hr
  2. filtrationthe mixture was then filtered under the reduced pressure
  3. concentrationThe filtrate was concentrated under the reduced pressure
  4. customthe residue was purified by column chromatography on silica gel [chloroform/methanol]

Sources & evidence

ORD record
ord-6b1b50f5cda149ff8919700ea85020be
Source dataset
uspto-grants-2007_05
Patent number
US07217722B2

Reaction notes

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