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Methanol → 3-Pyridinecarboxamide, 2-(((1,6-dihydro-6-oxo-3-pyridinyl)methyl)amino)-N-(3-(trifluoromethyl)phenyl)-

HRID 1168224
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HRID 1168224 반응식
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]
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참가 물질

5

반응물 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 10272439HCID 10272439, 화합물

생성물 1

HCID 101108113-Pyridinecarboxamide, 2-(((1,6-dihydro-6-oxo-3-pyridinyl)methyl)amino)-N-(3-(trifluoromethyl)phenyl)-

시약·촉매·용매 1

HCID 6212Chloroform용매

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온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-976e31d53d654a46b8fe6d84a571da45
출처 데이터셋
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06624174B2

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