1,1'-Carbonyldiimidazole → 3-Fluoro-N-methoxy-N-methylpicolinamide

HRID 573348노트

반응식

HRID 573348 반응식
[F:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[CH3:24][NH:25][O:26][CH3:27].CCN(C(C)C)C(C)C>C1COCC1>[F:1][C:2]1[C:3]([C:8]([N:25]([O:26][CH3:27])[CH3:24])=[O:10])=[N:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 27627863-Fluoropyridine-2-carboxylic acid

생성물 1

HCID 866889893-Fluoro-N-methoxy-N-methylpicolinamide수율 94.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of 3-fluoropicolinic acid (17.7 g) in THF (300 mL) was added CDI (22.4 g) at room temperature, and the mixture was stirred at room temperature for 30 min and heated to 50° C. After stirring at 50° C. for 1 h, the mixture was cooled to room temperature. To the mixture were added N,O-dimethylhydroxylamine hydrochloride (18.4 g) and DIPEA (32.9 mL) at room temperature, and the mixture was stirred at room temperature for 12 h. The mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt) to give the title compound (21.8 g).

후처리

  1. temperatureheated to 50° C
  2. stirringAfter stirring at 50° C. for 1 h
  3. temperaturethe mixture was cooled to room temperature
  4. stirringthe mixture was stirred at room temperature for 12 h
  5. concentrationThe mixture was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (AcOEt)

출처 및 근거

ORD 기록
ord-2b5f36724e144136bb7fb640ab418644
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029536B2

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