Ammonium Chloride → HCID 67448291, compound

HRID 2368076Notes

Reaction equation

HRID 2368076 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:30]=[CH:29][C:9]3[N:10]=[C:11]([N:13]4[CH2:18][CH2:17][CH:16]([O:19][CH2:20][C:21](N5CCOCC5)=[O:22])[CH2:15][CH2:14]4)[O:12][C:8]=3[CH:7]=2)[CH2:3][CH2:2]1.[CH3:31][Mg]Cl.[Cl-].[NH4+]>C1COCC1>[CH:1]1([CH2:4][O:5][C:6]2[CH:30]=[CH:29][C:9]3[N:10]=[C:11]([N:13]4[CH2:14][CH2:15][CH:16]([O:19][CH2:20][C:21](=[O:22])[CH3:31])[CH2:17][CH2:18]4)[O:12][C:8]=3[CH:7]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 67448287HCID 67448287, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 67448291HCID 67448291, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(cyclopropylmethoxy)-2-{4-[2-(morpholin-4-yl)-2-oxoethoxy]piperidin-1-yl}-1,3-benzoxazole (2.10 g) in THF (17 mL) was added methylmagnesium chloride (3.0 M THF solution, 5.06 mL), and the mixture was stirred at room temperature for 3 hr. Saturated aqueous ammonium chloride solution was added to the reaction mixture, 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 and the residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (1.31 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with 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 chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4ead761e259841dc8c9145890f5a0b06
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

Loading…