Sodium Bicarbonate → HCID 68998965, compound

HRID 1821386Notes

Reaction equation

HRID 1821386 reaction equation
C([O:3][C:4](=O)[C:5]([NH:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1/[CH:17]=[CH:18]/[C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][N:20]=1)=[O:9])=O)C.C(=O)([O-])O.[Na+]>CCCCCC.C(OCC)(=O)C>[NH:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19](/[CH:18]=[CH:17]/[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]2[C:4](=[O:3])[CH2:5][NH:7][C:8]2=[O:9])=[N:20]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 69002054HCID 69002054, compound

Product 1

HCID 68998965HCID 68998965, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

(E)-(3-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}ureido)oxoacetic acid ethyl ester (50 mg, 0.14 mmol) obtained in Step 1 was heated under reflux in a mixed solvent of 6.0 mol/L hydrochloric acid/acetone (1/1, 2.5 mL) under nitrogen atomosphere for 60 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate solution, extracted with ethyl acetate and the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=90/10) to obtain Compound 212 (38 mg, 87%).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationthe organic layer was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=90/10)

Sources & evidence

ORD record
ord-42c47b0fa251491c877c85c12f8d02ef
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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