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

HRID 1825840Notes

Reaction equation

HRID 1825840 reaction equation
C[O:2][CH:3](OC)[CH2:4][CH2:5][N:6]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([NH:15][C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:21][CH:20]=3)=[O:17])[CH:11]=[CH:12]2)=[N:7]1.Cl>CC(C)=O>[O:2]=[CH:3][CH2:4][CH2:5][N:6]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([NH:15][C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:21][CH:20]=3)=[O:17])[CH:11]=[CH:12]2)=[N:7]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 221388991-[2-(3,3-dimethoxypropyl)-2H-indazol-6-yl]-3-(4-phenoxyphenyl)urea

Product 1

HCID 221389081-[2-(3-oxopropyl)-2H-indazol-6-yl]-3-(4-phenoxyphenyl)urea

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 1-[2-(3,3-dimethoxypropyl)-2H-indazol-6-yl]-3-(4-phenoxyphenyl)urea (832 mg, 1.87 mmol) in acetone (15 mL) was added 2N aqueous HCl (7.5 mL) and the reaction was heated to 50 C for 3h. The heating bath was removed and the reaction was concentrated under reduced pressure to a volume of ˜5 mL. Et2O was added to the slurry with stirring and the mixture was filtered. The solid was washed with additional Et2O (10 mL) and air-dried to give 1-[2-(3-oxopropyl)-2H-indazol-6-yl]-3-(4-phenoxyphenyl)urea as a beige solid. 1H NMR (300 MHz, DMSO-D6) δ ppm 3.11 (t, J=6.27 Hz, 2 H), 4.67 (t, J=6.61 Hz, 2 H), 6.97 (m, 5 H), 7.10 (m, 1 H), 7.36 (m, 2 H), 7.48 (m, 2 H), 7.59 (m, 1 H), 7.82 (s, 1 H), 8.26 (s, 1 H), 8.70 (m, 2 H) and 9.75 (s, 1 H); MS (ESI) 399 (M−H)−.

Workup

  1. temperaturethe reaction was heated to 50 C for 3h
  2. customThe heating bath was removed
  3. concentrationthe reaction was concentrated under reduced pressure to a volume of ˜5 mL
  4. additionEt2O was added to the slurry
  5. filtrationthe mixture was filtered
  6. washThe solid was washed with additional Et2O (10 mL)
  7. customair-dried

Sources & evidence

ORD record
ord-b3551bbb0f1c4bc6876bcab92d16f466
Source dataset
uspto-grants-2006_05
Patent number
US07049307B2

Reaction notes

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