Methyl iodide → HCID 77105955, compound

HRID 1053123Notes

Reaction equation

HRID 1053123 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[O:11][C:10]([C:12]3[C:13]([NH2:25])=[N:14][CH:15]=[C:16]([C:18]4[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=4)[CH:17]=3)=[N:9][N:8]=2)[CH2:3][CH2:2]1.[H-].[Na+].[CH3:28]I>C1COCC1>[CH3:28][N:1]1[CH2:6][CH2:5][CH:4]([C:7]2[O:11][C:10]([C:12]3[C:13]([NH2:25])=[N:14][CH:15]=[C:16]([C:18]4[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=4)[CH:17]=3)=[N:9][N:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 90273387HCID 90273387, compound

Product 1

HCID 77105955HCID 77105955, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(5-piperidin-4-yl-[1,3,4]oxadiazol-2-yl)-5-p-tolyl-pyridin-2-ylamine (250 mg, 0.746 mmol) in THF (25 mL) was added NaH (55%) (48.8 mg, 1.119 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 1 h. Then MeI (95 mg, 0.671 mmol) was added at 0° C., and the reaction mixture was stirred at 0° C. for a further 3 h. The reaction mixture was then poured into ice-water (30 mL) and extracted with ethyl acetate (3×20 mL). The organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford crude compound. Crude compound was purified by preparative HPLC to afford the title compound as a pale yellow solid.

Workup

  1. stirringthe reaction mixture was stirred at 0° C. for a further 3 h
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customto afford crude compound
  7. customCrude compound was purified by preparative HPLC

Sources & evidence

ORD record
ord-90d94f4f95eb4b05812b398678d44979
Source dataset
uspto-grants-2016_07
Patent number
US09393248B1

Reaction notes

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