Hydrochloric Acid → HCID 67273579, compound

HRID 1696180Notes

Reaction equation

HRID 1696180 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[N:10][C:11]2[N:12]([N:21]=[C:22]([S:29](=[O:33])(=[O:32])[NH:30][CH3:31])[C:23]=2[C:24]([O:26]CC)=[O:25])[C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1.[OH-].[Na+].Cl>C(O)C.O1CCCC1>[C:24]([C:23]1[C:22]([S:29](=[O:33])(=[O:32])[NH:30][CH3:31])=[N:21][N:12]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH:9]=[N:10][C:11]=12)([OH:26])=[O:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67272922HCID 67272922, compound

Product 1

HCID 67273579HCID 67273579, compoundYield 109.7%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of the compound obtained in Example B1 (524 mg) in ethanol/tetrahydrofuran (7 mL/7 mL) was added an aqueous 2N sodium hydroxide solution (1.04 mL), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was weakly acidified with an aqueous 2N hydrochloric acid. The mixture was concentrated in vacuo and extracted with chloroform. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo to give 3-carboxy-6-(2-chlorophenyl)-7-(4-chlorophenyl)-2-(N-methylsulfamoyl)-pyrazolo[1,5-a]pyrimidine (543 mg) as a crude product.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-36b15ad5a94f479b8d70028adbda26d7
Source dataset
uspto-grants-2012_04
Patent number
US08163759B2

Reaction notes

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