Hydrochloric Acid → HCID 66856214, compound

HRID 1530011Notes

Reaction equation

HRID 1530011 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-a7d27f3f3a2f4b4696394e0c5244a693
Source dataset
uspto-grants-2015_07
Patent number
US09090601B2

Reaction notes

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