Hydrochloric Acid → HCID 22138906, compound

HRID 1825836Notes

Reaction equation

HRID 1825836 reaction equation
C[O:2][CH:3](OC)[CH2:4][N:5]1[CH:13]=[C:12]2[C:7]([CH:8]=[C:9]([NH:14][C:15]([NH: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)=[O:16])[CH:10]=[CH:11]2)=[N:6]1.Cl>CC(C)=O>[O:2]=[CH:3][CH2:4][N:5]1[CH:13]=[C:12]2[C:7]([CH:8]=[C:9]([NH:14][C:15]([NH: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)=[O:16])[CH:10]=[CH:11]2)=[N:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22138914HCID 22138914, compound

Product 1

HCID 22138906HCID 22138906, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 1-[2-(2,2-dimethoxyethyl)-2H-indazol-6-yl]-3-(4-phenoxyphenyl)urea (1.5 g, 3.47 mmol) in acetone (250 mL) was added 2N aqueous HCl (10 mL) and the reaction was heated to reflux for 72 hours. The mixture was allowed to cool and was concentrated under reduced pressure to a volume of 30 mL. Ethyl acetate (300 mL) was added to the slurry with stirring and the mixture was filtered. The solid was washed with additional ethyl acetate (10 mL) and air-dried to provide 1-[2-(2-oxo-ethyl)-2H-indazol-6-yl]-3-(4-phenoxyphenyl)urea. 1H NMR (300 MHz, DMSO-D6) δ ppm 5.38 (s, 2 H), 6.98 (m, 5 H), 7.09 (m, 1 H), 7.36 (m, 2 H), 7.49 (m, 2 H), 7.65 (m, 1 H), 7.87 (s, 1 H), 8.27 (s, 1 H), 8.87 (m, 2 H), 9.66 (s, 1 H); MS (ESI) 385 (M−H)−.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 72 hours
  3. temperatureto cool
  4. concentrationwas concentrated under reduced pressure to a volume of 30 mL
  5. additionEthyl acetate (300 mL) was added to the slurry
  6. filtrationthe mixture was filtered
  7. washThe solid was washed with additional ethyl acetate (10 mL)
  8. customair-dried

Sources & evidence

ORD record
ord-6fba8120536b4d9aaa868f48e2c563c2
Source dataset
uspto-grants-2006_05
Patent number
US07049307B2

Reaction notes

Loading…