Formaldehyde → HCID 18447150, compound

HRID 1269829Notes

Reaction equation

HRID 1269829 reaction equation
[CH3:1][C:2]1[C:10]([O:11][CH:12]2[CH2:17][CH2:16][CH2:15][NH:14][CH2:13]2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.C=O.[C:20]([BH3-])#N.[Na+].[OH-].[Na+]>CO.C(O)(=O)C>[CH3:1][C:2]1[C:10]([O:11][CH:12]2[CH2:17][CH2:16][CH2:15][N:14]([CH3:20])[CH2:13]2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 22934024HCID 22934024, compound

Product 1

HCID 18447150HCID 18447150, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Acetic acid (0.060 ml) was added to a methanolic solution (1.0 ml) of the 4-methyl-5-(piperidin-3-yloxy)-1H-indazole (46 mg, 0.20 mmol) obtained in Example 422, followed by adding thereto paraformaldehyde (30 mg, 1.0 mmol), and the resulting mixture was stirred at room temperature for 2 hours. Then, a solution of sodium cyanoborohydride (63 mg, 1.0 mmol) in methanol (1.0 ml) was added thereto and the resulting mixture was stirred at room temperature for 18 hours. After a 1N-aqueous sodium hydroxide solution (0.8 ml) was added to the reaction solution, the solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate/triethylamine=5/15/1) to obtain 4-methyl-5-[(1-methylpiperidin-3-yl)oxy]-1H-indazole (34 mg, 70%).

Workup

  1. additionby adding
  2. distillationthe solvent was distilled off under reduced pressure
  3. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate/triethylamine=5/15/1)

Sources & evidence

ORD record
ord-52357e798d35423a8e5d92940625004c
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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