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

HRID 1790146Notes

Reaction equation

HRID 1790146 reaction equation
C[O:2][CH:3](OC)[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:14][C:15](=[O:30])[CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:19][CH:18]=3)[CH:12]=2)[CH:7]=[N:6]1.Cl>CC(C)=O.C(OCC)(=O)C>[O:2]=[CH:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:14][C:15](=[O:30])[CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:19][CH:18]=3)[CH:12]=2)[CH:7]=[N:6]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22036601HCID 22036601, compound

Product 1

HCID 22036616N-[1-(2-oxoethyl)-1H-indazol-6-yl]-2-(4-phenoxyphenyl)acetamide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-[1-(2,2-dimethoxyethyl)-1H-indazol-6-yl]-2-(4-phenoxyphenyl)acetamide (2.0 g, 4.64 mmol) and 2N aqueous HCl (6.0 mL)in acetone (40 mL) was heated to reflux for 3 hours, cooled and diluted with ethyl acetate (300 mL). The layers were separated, and the organic was dried (Na2SO4), filtered, and concentrated under reduced pressure to provide N-[1-(2-oxoethyl)-1H-indazol-6-yl]-2-(4-phenoxyphenyl)acetamide as a beige solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.55 (s, 2 H), 3.7 (m, 2 H), 7.0 (m, 4 H), 7.1 (m, 2 H), 7.3 (m, 1 H), 7.4 (m, 4 H), 8.0 (s, 1 H), 8.15 (s, 1 H), 10.4 (s, 1 H), and 12.8 (s, 1 H); MS (ESI) 384.1 (M−H)−.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. temperaturecooled
  4. customThe layers were separated
  5. dry with materialthe organic was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a835ac973187491bb8f4f17c90a620d1
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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