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1,1'-Carbonyldiimidazole → 3,5-difluoro-N-methoxy-N-methylpicolinamide

HRID 573339
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HRID 573339 반응식
[F:1][C:2]1[C:3]([C:9]([OH:11])=O)=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[CH3:25][NH:26][O:27][CH3:28].CCN(C(C)C)C(C)C>C1COCC1>[F:1][C:2]1[C:3]([C:9]([N:26]([O:27][CH3:28])[CH3:25])=[O:11])=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1
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참가 물질

6

반응물 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 27832623,5-Difluoropyridine-2-carboxylic acid

생성물 1

HCID 866889883,5-difluoro-N-methoxy-N-methylpicolinamide수율 56.2%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
50 °C

실험 절차

To a suspension of 3,5-difluoropicolinic acid (3.5 g) in THF (70 ml) was added CDI (3.92 g) at room temperature. The mixture was stirred at room temperature for 30 min and at 50° C. for 1 h. After cooling to room temperature, N,O-dimethylhydroxylamine hydrochloride (3.22 g) and DIPEA (5.76 mL) were added. The mixture was stirred at room temperature for 12 h, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/AcOEt) to give the title compound (2.5 g).

후처리

  1. temperatureAfter cooling to room temperature
  2. stirringThe mixture was stirred at room temperature for 12 h
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/AcOEt)

출처 및 근거

ORD 기록
ord-6ff13c8000194879a37f3a0e314f8e53
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09029536B2

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