Dimethylformamide → 3-chloro-N-[2-hydroxy-5-(trifluoromethyl)pyridin-3-yl]isonicotinamide

HRID 884987

반응식

HRID 884987 반응식
[Cl:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].CN(C=O)C.[NH2:16][C:17]1[C:18]([OH:27])=[N:19][CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1.C(N(CC)CC)C>O>[Cl:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:16][C:17]1[C:18]([OH:27])=[N:19][CH:20]=[C:21]([C:23]([F:26])([F:24])[F:25])[CH:22]=1)=[O:5]

참가 물질

6

반응물 4

HCID 6228Dimethylformamide2회HCID 8471TriethylamineHCID 23157873-Amino-5-(trifluoromethyl)-1,2-dihydropyridin-2-oneHCID 204874993-Chloroisonicotinoyl chloride

생성물 1

HCID 1785221593-chloro-N-[2-hydroxy-5-(trifluoromethyl)pyridin-3-yl]isonicotinamide

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 0.88 g of 3-chloroisonicotinic acid, 5 ml of thionyl chloride and 20 mg of DMF was heated to reflux for three hours. After the reaction mixture was cooled to room temperature, it was concentrated under reduced pressure to give 3-chloroisonicotinic acid chloride. The resultant 3-chloroisonicotinic acid chloride and 4 ml of DMF was added dropwise to a mixture of 1.0 g of 3-amino-2-hydroxy-5-trifluoromethylpyridine, 1.14 g of triethylamine and 8 ml of DMF while ice-cooling. The reaction mixture was stirred at room temperature for one hour, and then stirred while heating at 50° C. for 30 minutes. The reaction mixture was cooled to room temperature, and then water was added to the reaction mixture, followed by extraction with ethyl acetate twice. The combined organic layers were washed with water and a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.87 g of 3-chloro-N-[2-hydroxy-5-(trifluoromethyl)pyridin-3-yl]isonicotinamide.

후처리

  1. temperaturecooling
  2. stirringstirred
  3. temperaturewhile heating at 50° C. for 30 minutes
  4. temperatureThe reaction mixture was cooled to room temperature
  5. extractionfollowed by extraction with ethyl acetate twice
  6. washThe combined organic layers were washed with water
  7. dry with materiala saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-a26a670b9b8f4bbf92222ed11f4f3d87
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242133B2

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