Hydrochloric Acid → HCID 58094953, compound

HRID 2282326Notes

Reaction equation

HRID 2282326 reaction equation
[CH3:1][C:2]1[C:10]([C:11]2[S:15][C:14]([C:16]([O:18]CC)=[O:17])=[C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:12]=2)=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[OH-].[Na+].C1COCC1.Cl>O.C(O)C>[CH3:1][C:2]1[C:10]([C:11]2[S:15][C:14]([C:16]([OH:18])=[O:17])=[C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:12]=2)=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58095118HCID 58095118, compound

Product 1

HCID 58094953HCID 58094953, compoundYield 102.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of ethyl 5-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-3-phenylthiophene-2-carboxylate (119 mg, 0.327 mmol), a 8N aqueous solution of sodium hydroxide (5 mL), THF (5 mL) and ethanol (10 mL) and water (1 mL) was stirred for 1 h at 70° C. The mixture was allowed to cool to 0° C. To the mixture, was added a 6N aqueous solution of hydrogen chloride to adjust ca pH 3-4. The mixture was extracted with EtOAc-THF mixed solvent and the organic phase was washed with brine and dried over anhydrous magnesium sulfate. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was washed with diisopropyl ether and dried under vacuum to yield the title compound (112 mg, over yield) as a pale yellow solid. 1H NMR (300 MHz, d6-DMSO) δ: 12.83 (br s, 1H), 8.80-8.65 (m, 1H), 8.00-7.93 (m, 1H), 7.61-7.53 (m, 2H), 7.44-7.36 (m, 4H), 7.28 (s, 1H), 7.02-6.95 (m, 1H), 2.60 (s, 3H).

Workup

  1. extractionThe mixture was extracted with EtOAc-THF mixed solvent
  2. washthe organic phase was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customInsoluble materials were removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. washThe residue was washed with diisopropyl ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-9e72293ad0a34f4cb7fce42d19097b7d
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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