Potassium Hydroxide → HCID 22933437, compound

HRID 1269971Notes

Reaction equation

HRID 1269971 reaction equation
[OH-:1].[K+].[NH:3]1[CH2:9][CH2:8][CH2:7][CH:6]([O:10][C:11]2[CH:19]=[CH:18][C:17]3[NH:16][N:15]=[CH:14][C:13]=3[C:12]=2[C:20]#[N:21])[CH2:5][CH2:4]1>C(O)(C)(C)C.C(O)C>[NH:3]1[CH2:9][CH2:8][CH2:7][CH:6]([O:10][C:11]2[CH:19]=[CH:18][C:17]3[NH:16][N:15]=[CH:14][C:13]=3[C:12]=2[C:20]([NH2:21])=[O:1])[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 22933562HCID 22933562, compound

Product 1

HCID 22933437HCID 22933437, compoundYield 25.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6386tert-ButanolSolvent

Procedure

Potassium hydroxide (powder, 100 mg) was added to a solution of the 5-(azepan-4-yloxy)-1H-indazole-4-carbonitrile (9.2 mg, 0.036 mmol) obtained in Example 691 in t-butanol (2 ml) at room temperature, and the resulting mixture was stirred for 30 hours with heating under reflux while maintaining the temperature. The reaction mixture was diluted with ethanol and filtered, and the filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was purified by a silica gel column chromatography (eluent: chloroform/methanol/28% aqueous ammonia) to obtain 5-(azepan-4-yloxy)-1H-indazole-4-carboxamide (2.5 mg, 25%).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. temperaturewhile maintaining the temperature
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customto obtain a crude product
  7. customThe crude product was purified by a silica gel column chromatography (eluent: chloroform/methanol/28% aqueous ammonia)

Sources & evidence

ORD record
ord-7a6fc11145ca45ba9270ab34f9dcae62
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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