Potassium Carbonate → HCID 11256064, compound

HRID 1711604Notes

Reaction equation

HRID 1711604 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[O:18][C:19]([C:22]([OH:24])=O)=[CH:20][CH:21]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=S(Cl)Cl.[NH2:29][OH:30].Cl.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[O:18][C:19]([C:22]([NH:29][OH:30])=[O:24])=[CH:20][CH:21]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 443297Hydroxyamine hydrochlorideHCID 10925187HCID 10925187, compound

Product 1

HCID 11256064HCID 11256064, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 962WaterSolvent

Procedure

A mixture of 1-benzyl-3-(5-hydroxycarbonyl-2-furyl)-1H-indazole (0.40 g, 1.257 mmol), DMF (cat., 2 drops) and SOCl2 (5 mL) was heated to reflux for 2 h. After cooling, the excess SOCl2 was removed under reduced pressure and the almost black oil was dissolved in DME (8 mL). A portion of this acid chloride solution (2 mL, approx. 0.314 mmol) was mixed with a solution of NH2OH.HCl (0.20 g, 2.88 mmol) and K2CO3 (excess) in H2O (2 mL) and allowed to stir at rt overnight A precipitate formed while stirring. The reaction mixture was poured onto water (50 mL) and extracted four times with EtOAc. The combined organic material was dried (MgSO4) and concentrated under reduced pressure to give the crude product (77.4 mg, 74%) as an orange/brown solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. temperatureAfter cooling
  4. customthe excess SOCl2 was removed under reduced pressure
  5. dissolutionthe almost black oil was dissolved in DME (8 mL)
  6. customformed
  7. stirringwhile stirring
  8. additionThe reaction mixture was poured onto water (50 mL)
  9. extractionextracted four times with EtOAc
  10. dry with materialThe combined organic material was dried (MgSO4)
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-efbea880b0df40f4be9f932fd2c7befb
Source dataset
uspto-grants-2010_09
Patent number
US07790761B2

Reaction notes

Loading…