Sodium Bicarbonate → HCID 69002059, compound

HRID 1821341Notes

Reaction equation

HRID 1821341 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](/[CH:17]=[CH:18]/[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N:25]2[CH2:30][CH2:29][N:28]([C:31](=[O:33])[CH3:32])[CH2:27][CH2:26]2)=[N:9]1)=O)(C)(C)C.C(OCC)(=O)C.Cl.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[C:31]([N:28]1[CH2:29][CH2:30][N:25]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2/[CH:18]=[CH:17]/[C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[NH:8][N:9]=2)[CH2:26][CH2:27]1)(=[O:33])[CH3:32]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 68999756HCID 68999756, compound

Product 1

HCID 69002059HCID 69002059, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of (E)-3-{2-[2-(4-acetylpiperazin-1-yl)phenyl]vinyl}indazole-1-carboxylic acid tert-butyl ester (41 mg, 0.094 mmol) obtained in Step 3 in ethyl acetate (1.5 mL) was added with 4.0 mol/L hydrogen chloride-ethyl acetate solution (0.082 mL, 0.32 mmol) and stirred at room temperature for 2.0 hours, followed by stirring under heating and reflux for 2.0 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate solution and ethyl acetate to separate the mixture into organic layer and aqueous layer and the aqueous layer was extracted with ethyl acetate 2 times. All organic layers were gathered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=90/10) to obtain Compound 133 (13 mg, 41%).

Workup

  1. stirringby stirring
  2. temperatureunder heating
  3. temperaturereflux for 2.0 hours
  4. customto separate the mixture into organic layer and aqueous layer
  5. extractionthe aqueous layer was extracted with ethyl acetate 2 times
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform/methanol=90/10)

Sources & evidence

ORD record
ord-359e5f47384c40d39ce32c058326ab7a
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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