Hydrochloric Acid → HCID 23630906, compound

HRID 917721Notes

Reaction equation

HRID 917721 reaction equation
[F:1][C:2]1[CH:27]=[C:26]([I:28])[CH:25]=[CH:24][C:3]=1[NH:4][C:5]1[C:6]([C:21]([NH2:23])=[O:22])=[CH:7][N:8]([CH2:12][CH2:13][O:14]C2CCCCO2)[C:9](=[O:11])[CH:10]=1.Cl>CCO.O>[F:1][C:2]1[CH:27]=[C:26]([I:28])[CH:25]=[CH:24][C:3]=1[NH:4][C:5]1[C:6]([C:21]([NH2:23])=[O:22])=[CH:7][N:8]([CH2:12][CH2:13][OH:14])[C:9](=[O:11])[CH:10]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 23631097HCID 23631097, compound

Product 1

HCID 23630906HCID 23630906, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-(2-Fluoro-4-iodoanilino)-6-oxo-1-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1,6-dihydro-3-pyridinecarboxamide (118 mg, 0.24 mmol) was dissolved in EtOH (8 mL), to which was added 1 M HCl (2 mL). This mixture was stirred at R.T. for 2 h., then diluted with water (80 mL). The resulting solution was extracted with EtOAc (3×40 mL), then the combined EtOAc fractions washed with water (2×50 mL) and brine (50 mL), then dried (Na2SO4). Removal of the solvent under reduced pressure afforded 4-(2-fluoro-4-iodoanilino)-1-(2-hydroxyethyl)-6-oxo-1,6-dihydro-3-pyridinecarboxamide as a white solid (95 mg, 97%), m.p. (EtOAc/MeOH) 212-215° C. 1H NMR [(CD3)2SO, 400 MHz] δ 10.45 (s, 1H), 8.27 (s, 1H), 7.94 (br s, 1H), 7.74 (dd, J=10.1, 1.7 Hz, 1H), 7.57 (br d, J=8.6 Hz, 1H), 7.48 (br s, 1H), 7.29 (t, J=8.5 Hz, 1H), 5.55 (s, 1H), 4.93 (t, J=5.3 Hz, 1H), 3.85 (t, J=5.5 Hz, 2H), 3.60 (q, J=5.4 Hz, 2H). Anal. Calcd for C14H13FIN3O3: C, 40.3; H, 3.1; N, 10.1. Found: C, 40.4; H, 2.9; N, 9.8.

Workup

  1. extractionThe resulting solution was extracted with EtOAc (3×40 mL)
  2. washthe combined EtOAc fractions washed with water (2×50 mL) and brine (50 mL)
  3. dry with materialdried (Na2SO4)
  4. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-0d1ece6a05da4653aa47754a79329072
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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