Hydrochloric Acid → HCID 58484014, compound

HRID 2368077Notes

Reaction equation

HRID 2368077 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:25]=[CH:24][C:9]3[N:10]=[C:11]([N:13]4[CH2:18][CH2:17][CH:16]([O:19][CH2:20][C:21](=O)[CH3:22])[CH2:15][CH2:14]4)[O:12][C:8]=3[CH:7]=2)[CH2:3][CH2:2]1.[O:26]1[CH:30]=[CH:29][C:28]([NH2:31])=[N:27]1.[B][B][B][B][B][B][B][B][B][B].Cl>CO.C(O)(=O)C>[CH:1]1([CH2:4][O:5][C:6]2[CH:25]=[CH:24][C:9]3[N:10]=[C:11]([N:13]4[CH2:18][CH2:17][CH:16]([O:19][CH2:20][CH:21]([NH:31][C:28]5[CH:29]=[CH:30][O:26][N:27]=5)[CH3:22])[CH2:15][CH2:14]4)[O:12][C:8]=3[CH:7]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 18102163-IsoxazolamineHCID 67448291HCID 67448291, compoundHCID 178419135HCID 178419135, compound

Product 1

HCID 58484014HCID 58484014, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 1-({1-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]piperidin-4-yl}oxy)propan-2-one (400 mg) and isoxazol-3-amine (0.129 mL) in methanol (6 mL) and acetic acid (0.300 mL) was added decaborane (213 mg), and the mixture was stirred at room temperature for 3 hr. 1M Hydrochloric acid was added to the reaction mixture, and the mixture was stirred at room temperature for 30 min, and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (hexane/ethyl acetate). The obtained residue was applied to preparative HPLC (C18, mobile phase: water/acetonitrile (containing 0.1% TFA)). Saturated aqueous sodium hydrogen carbonate solution was added to the obtained fraction, and the mixture was extracted with ethyl acetate and the extract was dried over anhydrous sodium sulfate. The residue was concentrated under reduced pressure to give the title compound (126 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 30 min
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate)
  7. additionSaturated aqueous sodium hydrogen carbonate solution was added to the obtained fraction
  8. extractionthe mixture was extracted with ethyl acetate
  9. dry with materialthe extract was dried over anhydrous sodium sulfate
  10. concentrationThe residue was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8e4e4bb52c954f8bb543fe7c83bf27db
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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