Ethyl formate → 5-Fluoro-6-oxo-2-(quinolin-6-ylamino)-1,6-dihydropyridin-3-carbonitrile

HRID 340439노트

반응식

HRID 340439 반응식
[CH:1](OCC)=O.[H-].[Na+].C([O:11][CH2:12][CH2:13][F:14])(=O)C.[C:15]([CH2:17][C:18]([NH:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[N:27]=[CH:26][CH:25]=[CH:24]2)=[NH:19])#[N:16]>C(O)C.CCCCCC>[F:14][C:13]1[C:12](=[O:11])[NH:19][C:18]([NH:20][C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[N:27]=[CH:26][CH:25]=[CH:24]3)=[C:17]([C:15]#[N:16])[CH:1]=1

참가 물질

7

반응물 4

HCID 8025Ethyl formateHCID 10016Ethanol, 2-fluoro-, 1-acetateHCID 24758Sodium hydrideHCID 178511140HCID 178511140, 화합물

생성물 1

HCID 686063515-Fluoro-6-oxo-2-(quinolin-6-ylamino)-1,6-dihydropyridin-3-carbonitrile

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 8058Hexane용매

실험 절차

Ethyl formate (16.1 ml) was added to a hexane (40 ml) suspension containing sodium hydride (60% in oil, 2.4 g) at room temperature, and then fluoroethyl acetate (3.86 ml) was added dropwise under ice cooling, followed by stirring at room temperature for 15 minutes. Ethanol (50 ml) was added to the reaction mixture, and then an ethanol (50 ml) solution containing 2-cyano-N-(quinolin-6-yl)acetamidine (4.20 g) was added dropwise, followed by stirring at 80° C. for 2 hours. The reaction mixture was cooled to room temperature. Then, solid matter was collected by filtration and washed with ethyl acetate, and a yellow solid of 5-fluoro-6-oxo-2-(quinolin-6-ylamino)-1,6-dihydropyridin-3-carbonitrile (3.71 g) was thus obtained.

후처리

  1. additionwas added dropwise
  2. stirringby stirring at 80° C. for 2 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationThen, solid matter was collected by filtration
  5. washwashed with ethyl acetate

출처 및 근거

ORD 기록
ord-0af78f720882434f8794c4e806fad912
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895585B2

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