Sulfuric Acid → HCID 10275412, compound

HRID 639573Notes

Reaction equation

HRID 639573 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])[CH:5]=[CH:4][C:3]=1[CH2:15][C:16]([C:18]1[N:22]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[N:21]=[C:20]([C:31]#[N:32])[CH:19]=1)=[O:17].S(O)(O)(=O)=[O:34].C(OCC)(=O)C>O>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])[CH:5]=[CH:4][C:3]=1[CH2:15][C:16]([C:18]1[N:22]([C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)[N:21]=[C:20]([C:31]([NH2:32])=[O:34])[CH:19]=1)=[O:17]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 22240395HCID 22240395, compound

Product 1

HCID 10275412HCID 10275412, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Part I. To 5-{[2-fluoro-4-(2-oxo-1(2H)-pyridinyl)-phenyl]acetyl}-1-(4-methoxyphenyl)-1H-pyrazole-3-carbonitrile (75 mg, 0.175 mmol) was added concentrated aqueous dihydrogen sulfate (4.5 mL). After 2 h, the reaction was poured into ethyl acetate (50 mL) and water (50 mL), and the layers were separated. The organic layer was washed with saturated aqueous sodium chloride (50 mL), dried over sodium sulfate, and concentrated to dryness. The resulting residue was purified by radial chromatography (2% methyl alcohol in dichloromethane) to afford 5-{[2-fluoro-4-(2-oxo-1(2H)-pyridinyl)phenyl]acetyl}-1-(4-methoxyphenyl)-1H-pyrazole-3-carboxamide (32 mg, 41%) as a white solid upon lyophilization from 10% acetonitrile in water. LC/MS (ESI+): 448.2 (M+H)+. 1H NMR (CD3OD) δ 7.70 (s, 1H), 7.60 (m, 2H), 7.43 (t, 1H), 7.16-7.32 (m, 4H), 6.97 (d, 2H), 6.60 (d, 1H), 6.45 (t, 1H), 4.40 (s, 2H), 3.83 (s, 3H).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with saturated aqueous sodium chloride (50 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness
  5. customThe resulting residue was purified by radial chromatography (2% methyl alcohol in dichloromethane)

Sources & evidence

ORD record
ord-09e0315be9b247a9969a7879ef42d52f
Source dataset
uspto-grants-2010_04
Patent number
US07691846B2

Reaction notes

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