Hydrochloric Acid → HCID 67096440, compound

HRID 2075961Notes

Reaction equation

HRID 2075961 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([O:32][CH3:33])=[CH:11][C:12]([C:26]2[N:30]=[C:29]([CH3:31])[O:28][N:27]=2)=[C:13]([C:15](=[O:25])[C:16]([NH:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:17])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:37].Cl>C(OCC)(=O)C.CN(C)C=O>[CH2:1]([O:8][C:9]1[C:10]([O:32][CH3:33])=[CH:11][C:12]([C:26]2[N:30]=[C:29]([CH3:31])[O:28][N:27]=2)=[C:13]([C:15](=[O:25])[C:16]([N:18]([CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[CH3:37])=[O:17])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59565705HCID 59565705, compound

Product 1

HCID 67096440HCID 67096440, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-[5-benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)phenyl]N-cyclohexyl-2-oxoacetamide (reference example 14-15) (860 mg) and N,N-dimethylformamide (6 mL) was added sodium hydride (60%, 92 mg). After stirring at room temperature for 20 minutes, iodomethane (0.48 mL) was added to the mixture. After stirring at room temperature for 8 hours, the mixture was poured into a mixture of 2 mol/L hydrochloric acid and ice-water. Ethyl acetate was added to the mixture. The separated organic layer was washed with water, an aqueous solution of sodium bicarbonate and brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 0%-50% ethyl acetate/hexane, gradient elution) to give the title compound (605 mg).

Workup

  1. stirringAfter stirring at room temperature for 8 hours
  2. washThe separated organic layer was washed with water
  3. dry with materialan aqueous solution of sodium bicarbonate and brine successively, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: 0%-50% ethyl acetate/hexane, gradient elution)

Sources & evidence

ORD record
ord-5bbaef055ae24492a37a38e987e2d5c7
Source dataset
uspto-grants-2011_04
Patent number
US07923462B2

Reaction notes

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