Hydrochloric Acid → N-[1-(3-oxopropyl)-1H-indazol-6-yl]-2-(4-phenoxyphenyl)acetamide

HRID 1790149Notes

Reaction equation

HRID 1790149 reaction equation
C[O:2][CH:3](OC)[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH:15][C:16](=[O:31])[CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)[CH:13]=2)[CH:8]=[N:7]1.Cl>CC(C)=O>[O:2]=[CH:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH:15][C:16](=[O:31])[CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)[CH:13]=2)[CH:8]=[N:7]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22036559N-[1-(3,3-dimethoxypropyl)-1H-indazol-6-yl]-2-(4-phenoxyphenyl)acetamide

Product 1

HCID 22036564N-[1-(3-oxopropyl)-1H-indazol-6-yl]-2-(4-phenoxyphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of N-[1-(3,3-dimethoxypropyl)-1H-indazol-6-yl]-2-(4-phenoxyphenyl)acetamide (500 mg, 1.12 mmol) and 2N aqueous HCl (2.5 mL) in acetone (5 mL) was heated to 50 C for 3 hours, cooled to room temperature and concentrated under reduced pressure to a volume of ˜2 mL. Diethyl ether (15 mL) was added with stirring and the mixture was filtered. The filtered solid was washed with additional diethyl ether (10 mL) and air-dried to provide the title compound. MS (ESI) 398 (M−H)−.

Workup

  1. temperaturewas heated to 50 C for 3 hours
  2. concentrationconcentrated under reduced pressure to a volume of ˜2 mL
  3. additionDiethyl ether (15 mL) was added
  4. filtrationthe mixture was filtered
  5. washThe filtered solid was washed with additional diethyl ether (10 mL)
  6. customair-dried

Sources & evidence

ORD record
ord-3e5ebf92fa5340759bf9af3ca85b7367
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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