HCID 178418573, compound → HCID 178472350, compound

HRID 2368140Notes

Reaction equation

HRID 2368140 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:30]=[CH:29][C:9]3[N:10]=[C:11]([C@H:13]4[CH2:18][CH2:17][C@H: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]Br>C1COCC1.C1(C)C=CC=CC=1.C1COCC1>[CH:1]1([CH2:4][O:5][C:6]2[CH:30]=[CH:29][C:9]3[N:10]=[C:11]([C@H:13]4[CH2:18][CH2:17][C@H:16]([O:19][CH2:20][C:21](=[O:22])[CH3:31])[CH2:15][CH2:14]4)[O:12][C:8]=3[CH:7]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 178418573HCID 178418573, compoundHCID 178521451HCID 178521451, compound

Product 1

HCID 178472350HCID 178472350, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22635083Tetrahydrofuran tolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-(cyclopropylmethoxy)-2-[trans-4-(2-(morpholin-4-yl)-2-oxoethoxy)cyclohexyl]-1,3-benzoxazole (427 mg) in THF (5 mL) was added a solution (1.5 M, 1.37 mL) of methylmagnesium bromide in toluene/THF under ice-cooling. The reaction mixture was stirred at 0° C. for 1 hr, and extracted with ethyl acetate and 1M hydrochloric acid. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (260 mg).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate and 1M hydrochloric acid
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-78642e355bbc42b4b646759a1769ae27
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

Loading…