Hydrochloric Acid → HCID 59853093, compound

HRID 1670234Notes

Reaction equation

HRID 1670234 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)[CH:10]=1.Cl>CO>[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)[CH:10]=2)=[C:2]([F:1])[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59853071HCID 59853071, compound

Product 1

HCID 59853093HCID 59853093, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-(3-fluoro-4-(2-(4-fluorophenylamino)pyridin-4-yloxy)phenyl)acetamide (18 mg, 0.051 mmol), 6 M HCl (0.1 mL, 0.60 mmol) and MeOH (1.5 mL) was heated at reflux for 2 h. The mixture was concentrated in vacuo and the residue made basic with saturated aq. NaHCO3 solution then extracted with EtOAc. The extract was dried (MgSO4) and concentrated in vacuo to give the title compound (14 mg, 88%) as a red gum. 1H NMR (DMSO-d6) δ 8.97 (s, 1H), 7.98 (d, 1H, J=5.8 Hz), 7.64-7.60 (m, 2H), 7.05 (dd, 2H, J=9.1, 8.8 Hz), 6.97 (dd, 1H, J=9.4, 8.8 Hz), 6.51 (dd, 1H, J=13.3, 2.6 Hz), 6.40 (ddd, 2H, J=9.0, 6.2, 2.1 Hz), 6.08 (d, 1H, J=2.0 Hz), 5.44 (br s, 2H); MS (ESI+) m/z 314.17 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. concentrationThe mixture was concentrated in vacuo
  4. extractionthen extracted with EtOAc
  5. dry with materialThe extract was dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6604cc1942b8481d8d0b917e82e456d9
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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