Hydrochloric Acid → HCID 118378912, compound

HRID 931028Notes

Reaction equation

HRID 931028 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[O:12][C:11]([Si](C(C)C)(C(C)C)C(C)C)=[N:10][CH:9]=2)[N:5]2[N:23]=[CH:24][C:25]([C:26]([N:28]3[CH2:33][C@@H:32]4[CH2:34][C@H:29]3[CH2:30][O:31]4)=[O:27])=[C:4]2[CH:3]=1.Cl.[Cl-].[NH4+]>C1COCC1>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[O:12][CH:11]=[N:10][CH:9]=2)[N:5]2[N:23]=[CH:24][C:25]([C:26]([N:28]3[CH2:33][C@@H:32]4[CH2:34][C@H:29]3[CH2:30][O:31]4)=[O:27])=[C:4]2[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 131735153HCID 131735153, compound

Product 1

HCID 118378912HCID 118378912, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl(7-iodo-5-methylpyrazolo[1,5-a]pyridin-3-yl)methanone (300 mg), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(triisopropylsilyl)oxazole (330 mg), tetrakis(triphenylphosphine)palladium(0) (90 mg) and 3N aqueous potassium carbonate solution (0.522 mL) in DME (3 mL) was stirred with microwave irradiation at 120° C. for 30 min. The reaction mixture was diluted with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give (5-methyl-7-(2-(triisopropylsilyl)-1,3-oxazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)((1S,4S)-2-oxa-5-azabicyclo[2.2.1]hept-5-yl)methanone. The obtained (5-methyl-7-(2-(triisopropylsilyl)-1,3-oxazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)((1S,4S)-2-oxa-5-azabicyclo[2.2.1]hept-5-yl)methanone was dissolved in THF (3 mL), and 1N hydrochloric acid was added thereto. The reaction mixture was stirred at room temperature for 30 min, saturated aqueous ammonium chloride solution was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane), and the obtained solid was recrystallized from ethyl acetate/hexane to give the title compound (83 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)
  6. customthe obtained solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-01a49f991f7a474b8393074183a7b792
Source dataset
uspto-grants-2016_03
Patent number
US09296746B2

Reaction notes

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