Bicarbonate Ion → HCID 22240395, compound

HRID 2222604Notes

Reaction equation

HRID 2222604 reaction equation
[C:1]([C:3]1[CH:7]=[C:6]([C:8](=[O:27])[CH:9]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]3=[O:25])=[CH:15][C:14]=2[F:26])C([O-])=O)[N:5]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[N:4]=1)#[N:2].CO.S(O)(O)(=O)=O.C(=O)([O-])O>C(OCC)(=O)C>[F:26][C:14]1[CH:15]=[C:16]([N:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]2=[O:25])[CH:17]=[CH:18][C:13]=1[CH2:9][C:8]([C:6]1[N:5]([C:28]2[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=2)[N:4]=[C:3]([C:1]#[N:2])[CH:7]=1)=[O:27]

Participants

6

Reactant 4

HCID 769Bicarbonate IonHCID 887MethanolHCID 1118Sulfuric AcidHCID 22240483HCID 22240483, compound

Product 1

HCID 22240395HCID 22240395, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

Part H. To 3-[3-cyano-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]-2-[2-fluoro-4-(2-oxo-1(2H)-pyridinyl)phenyl]-3-oxopropanoate (100 mg, 0.210 mmol) was added methyl alcohol (1.5 mL) and 4M aqueous dihydrogen sulfate (0.50 mL). The reaction was then warmed to reflux. After 4 days, the reaction was cooled to 23° C., and the resulting white suspension was poured into saturated aqueous hydrogen carbonate (50 mL) and ethyl acetate (50 mL). The layers were separated and the aqueous layer was washed with ethyl acetate (3×25 mL). The combined organic layers were washed with saturated aqueous sodium chloride, dried over sodium sulfate, and concentrated to afford 5-{[2-fluoro-4-(2-oxo-1(2H)-pyridinyl)phenyl]acetyl}-1-(4-methoxyphenyl)-1H-pyrazole-3-carbonitrile (75 mg, 85%)as a pale yellow oil. LC/MS (ESI+): 429.0 (M+H)+.

Workup

  1. temperatureThe reaction was then warmed to reflux
  2. customThe layers were separated
  3. washthe aqueous layer was washed with ethyl acetate (3×25 mL)
  4. washThe combined organic layers were washed with saturated aqueous sodium chloride
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c2e9850aacff4111b5fdf80f3bca46e6
Source dataset
uspto-grants-2008_05
Patent number
US07371761B2

Reaction notes

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