Hydrochloric Acid → HCID 59852945, compound

HRID 2373989Notes

Reaction equation

HRID 2373989 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:23]C(=O)C)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[N:10]=1.Cl.CO>CCOC(C)=O>[NH2:23][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[N:10]=2)=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 59853019HCID 59853019, compound

Product 1

HCID 59852945HCID 59852945, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(3-fluoro-4-(2-(4-fluorophenylamino)pyrimidin-4-yloxy)phenyl)acetamide (32 mg, 0.09 mmol), 6 M HCl (0.2 mL) and MeOH (2 mL) was heated at reflux for 2 h. The mixture was cooled, diluted with EtOAc (20 mL), washed with saturated NaHCO3 solution and brine, dried (MgSO4), and concentrated in vacuo. Flash chromatography on SiO2 using 30-40% EtOAc in hexanes containing 1% Et3N gave the title compound (15 mg, 46%) as a white solid. 1H NMR (DMSO-d6) δ 9.55 (s, 1H), 8.25 (d, 1H, J=5.5 Hz), 7.43 (br s, 2H), 6.92-6.85 (m, 3H), 6.45 (dd, 1H, J=13.5, 2.1 Hz), 6.38-6.35 (m, 2H), 5.35 (br s, 2H). MS(ESI+) m/z 315.17 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. temperatureThe mixture was cooled
  4. washwashed with saturated NaHCO3 solution and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d420f4623aa74aaa962e793533c1e86f
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

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