Hydrochloric Acid → HCID 66856214, compound

HRID 2282173Notes

Reaction equation

HRID 2282173 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([C:17]3[C:18]([CH3:26])=[N:19][N:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=34)[S:11][C:12]=2[C:13]([O:15]C)=[O:14])[CH:5]=[CH:6][CH:7]=1.O1CCCC1.[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([C:17]3[C:18]([CH3:26])=[N:19][N:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=34)[S:11][C:12]=2[C:13]([OH:15])=[O:14])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66855408HCID 66855408, compound

Product 1

HCID 66856214HCID 66856214, compoundYield 110.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 4-(3-fluorophenyl)-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,3-thiazole-5-carboxylate (120 mg, 0.27 mmol) purified above in methanol (15 mL) and tetrahydrofuran (25 mL) was added 8N aqueous sodium hydroxide solution (6 mL), and the mixture was stirred at 70° C. for 1 hr. The reaction solution was cooled to 0° C., 6N hydrochloric acid was added to adjust the solution to about pH 3.0, and the reaction solution was extracted with ethyl acetate (100 mL×2). The collected organic layer was dried over anhydrous magnesium sulfate, the insoluble material was filtered off, and the filtrate was concentrated to give the title compound (105 mg, 91%) as a yellow solid.

Workup

  1. temperatureThe reaction solution was cooled to 0° C.
  2. extractionthe reaction solution was extracted with ethyl acetate (100 mL×2)
  3. dry with materialThe collected organic layer was dried over anhydrous magnesium sulfate
  4. filtrationthe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a61c55cb8df34c44a05c7755b0c4d4a2
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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