Methanol → 352227-91-9

HRID 1168224Notes

Reaction equation

HRID 1168224 reaction equation
C[O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][NH:10][C:11]2[C:16]([C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:5][CH:4]=1.C[Si](I)(C)C.CO>C(Cl)(Cl)Cl>[NH:8]1[CH:7]=[C:6]([CH2:9][NH:10][C:11]2[C:16]([C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:28])[F:29])[CH:21]=3)=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:5]=[CH:4][C:3]1=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 10272439HCID 10272439, compound

Product 1

HCID 10110811352227-91-9

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-[(6-Methoxypyrid-3-yl)methylamino]-N-[3-(trifluoromethyl)phenyl]-3-pyridinecarboxamide (Example 4; 1.4 g, 3.65 mmol) and trimethylsilyl iodide (Fluka, Buchs, Switzerland; 1.4 mL, 10.3 mmol) in chloroform (30 mL) is stirred at 60° C. for 28 hours. The cooled mixture is then treated with methanol (2 mL) and stirred at room temperature for 10 minutes. The solvent is evaporated off under reduced pressure and the residue is treated with an aqueous solution of ammonia (100 mL of 10%) and extracted with ethyl acetate (3×100 mL). The combined extracts are washed with saturated aqueous sodium chloride (50 mL), dried (Na2SO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by recrystallisation from hot ethyl acetate to give the title compound as a colourless crystalline solid, ma.p. 200-202° C.

Workup

  1. stirringstirred at room temperature for 10 minutes
  2. customThe solvent is evaporated off under reduced pressure
  3. additionthe residue is treated with an aqueous solution of ammonia (100 mL of 10%)
  4. extractionextracted with ethyl acetate (3×100 mL)
  5. washThe combined extracts are washed with saturated aqueous sodium chloride (50 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent is evaporated off under reduced pressure
  9. customto yield the crude product which
  10. customis purified by recrystallisation from hot ethyl acetate

Sources & evidence

ORD record
ord-976e31d53d654a46b8fe6d84a571da45
Source dataset
uspto-grants-2003_09
Patent number
US06624174B2

Reaction notes

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