Methyl iodide → HCID 77105959, compound

HRID 1053126Notes

Reaction equation

HRID 1053126 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([C:16]3[O:17][C:18]([CH:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)=[N:19][N:20]=3)[C:12]([NH2:15])=[N:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[CH3:29]I>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([C:16]3[O:17][C:18]([CH:21]4[CH2:26][CH2:25][N:24]([CH3:29])[CH2:23][CH2:22]4)=[N:19][N:20]=3)[C:12]([NH2:15])=[N:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 77105958HCID 77105958, compound

Product 1

HCID 77105959HCID 77105959, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-(3-methoxyphenyl)-3-[5-(4-piperidyl)-1,3,4-oxadiazol-2-yl]-pyridin-2-amine (150 mg, 0.42 mmol) in THF (20 mL) was added 60% NaH (25.0 mg, 064 mmol) at 0° C. and the reaction mixture was stirred at 0° C. for 10 min. Then MeI (54.5 mg, 0.38 mmol) was added at 0° C. and stirred the reaction mixture at 0° C. for 2 h. The reaction mixture was poured into ice-water (30 mL), extracted with ethyl acetate (3×20 mL), organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. Crude product was purified by preparative TLC to afford the title compound as a yellow solid.

Workup

  1. stirringstirred the reaction mixture at 0° C. for 2 h
  2. extractionextracted with ethyl acetate (3×20 mL), organic layer
  3. washwas washed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customCrude product was purified by preparative TLC

Sources & evidence

ORD record
ord-eb4ebd7ee501489287698ea9467e49c8
Source dataset
uspto-grants-2016_07
Patent number
US09393248B1

Reaction notes

Loading…