Propanal → HCID 22933631, compound

HRID 1269740Notes

Reaction equation

HRID 1269740 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][N:14]=[CH:13]3)=[O:9])[CH2:3][CH2:2]1.[CH:19](=O)[CH2:20][CH3:21].C([BH3-])#N.[Na+].[OH-].[Na+]>CO.C(O)(=O)C>[CH2:19]([N:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][N:14]=[CH:13]3)=[O:9])[CH2:3][CH2:2]1)[CH2:20][CH3:21]

Participants

7

Reactant 4

HCID 527PropanalHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 22933392HCID 22933392, compound

Product 1

HCID 22933631HCID 22933631, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

Acetic acid (0.048 ml) was added to a solution of the N-(4-piperidinyl)-1H-indazole-5-carboxamide (40.0 mg, 0.164 mmol) obtained in Example 58 in methanol (1.2 ml), and the resulting solution was maintained at room temperature for 30 minutes. Propionaldehyde (48.0 mg, 0.826 mmol) was added to the solution and the resulting mixture was maintained at room temperature for another 2 hours. Then, a solution of sodium cyanoborohydride (51.5 mg, 0.820 mmol) in methanol (3.0 ml) was added dropwise thereto, and the resulting mixture was stirred for 18 hours while being maintained at room temperature. A 1N-aqueous sodium hydroxide solution (0.8 ml) was added to the reaction solution, and the resulting mixture was stirred while being maintained at room temperature, and then was concentrated to dryness. The resulting crude product residue was purified by a silica gel column chromatography (eluent: chloroform/methanol/aqueous ammonia=20/1/0.1) to obtain N-(1-propylpiperidin-4-yl)-1H-indazole-5-carboxamide (31 mg, 46%).

Workup

  1. temperaturethe resulting mixture was maintained at room temperature for another 2 hours
  2. temperaturewhile being maintained at room temperature
  3. stirringthe resulting mixture was stirred
  4. temperaturewhile being maintained at room temperature
  5. concentrationwas concentrated to dryness
  6. customThe resulting crude product residue was purified by a silica gel column chromatography (eluent: chloroform/methanol/aqueous ammonia=20/1/0.1)

Sources & evidence

ORD record
ord-0e2dd5d292f948a4ababb5443228b9bb
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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