4-Methyl-1,2-oxazol-3-amine → HCID 58483990, compound

HRID 2368088Notes

Reaction equation

HRID 2368088 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.[CH3:26][C:27]1[C:28]([NH2:32])=[N:29][O:30][CH:31]=1.[B][B][B][B][B][B][B][B][B][B]>CO.C(O)(=O)C.C(OCC)(=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[CH2:14][CH2:15][CH:16]([O:19][CH2:20][CH:21]([NH:32][C:28]5[C:27]([CH3:26])=[CH:31][O:30][N:29]=5)[CH3:22])[CH2:17][CH2:18]4)[O:12][C:8]=3[CH:7]=2)[CH2:2][CH2:3]1

Participants

7

Reactant 3

HCID 137950474-Methyl-1,2-oxazol-3-amineHCID 67448291HCID 67448291, compoundHCID 178419135HCID 178419135, compound

Product 1

HCID 58483990HCID 58483990, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-({1-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]piperidin-4-yl}oxy)propan-2-one (50 mg) and 4-methylisoxazol-3-amine (21.4 mg) in methanol (1 mL) and acetic acid (50 μL) was added decaborane (26.6 mg), and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed with distilled water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (NH, hexane/ethyl acetate). 1M Hydrochloric acid was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (42.1 mg).

Workup

  1. washwashed with distilled water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel chromatography (NH, hexane/ethyl acetate)
  5. addition1M Hydrochloric acid was added
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-41bd571b42874f50ad12ae553add1a77
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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