Hydrochloric Acid → HCID 71178941, compound

HRID 2409267Notes

Reaction equation

HRID 2409267 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[N:10]([N:21]=[CH:22][C:23]=2[S:24]([OH:27])(=O)=[O:25])[C:11]=1[NH:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[CH3:20])=[O:5])[CH3:2].S(Cl)(Cl)=O.CN(C=O)C.[C:37]([NH2:41])([CH3:40])([CH3:39])[CH3:38].C(N(CC)CC)C.Cl>ClCCCl>[C:37]([NH:41][S:24]([C:23]1[CH:22]=[N:21][N:10]2[C:11]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=3[CH3:20])=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:7]=[N:8][C:9]=12)(=[O:25])=[O:27])([CH3:40])([CH3:39])[CH3:38]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 86681882HCID 86681882, compound

Product 1

HCID 71178941HCID 71178941, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

6-Ethoxycarbonyl-7-(4-fluoro-2-methylphenylamino)pyrazolo[1,5-a]pyrimidine-3-sulfonic acid (0.400 g, 1.01 mmol) obtained in step 2 was dissolved in 1,2-dichloroethane (4 mL), thionyl chloride (0.29 mL, 4.05 mmol) and DMF (0.024 mL, 0.304 mmol) were added, and the mixture was heated under reflux for 2 hr. The reaction mixture was concentrated under reduced pressure, the obtained residue was dissolved in methylene chloride (4 mL), tert-butylamine (0.21 mL, 2.02 mmol) and triethylamine (0.35 mL, 2.53 mmol) were added dropwise and the mixture was stirred at room temperature for 2 hr. 1 mol/L hydrochloric acid was added dropwise to the reaction mixture, and the mixture was extracted 3 times with chloroform. The combined organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (0.29 g, 63%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe obtained residue was dissolved in methylene chloride (4 mL)
  5. extractionthe mixture was extracted 3 times with chloroform
  6. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-91435e041e2a4a6fbfe78dace5c4d7b0
Source dataset
uspto-grants-2014_08
Patent number
US08815874B2

Reaction notes

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