Diisopropylethylamine → N'-(5-bromopyridin-2-yl)-2-(6-chloropyridazin-3-yl)-2,2-difluoroacetohydrazide

HRID 1925136노트

반응식

HRID 1925136 반응식
[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([F:15])([F:14])[C:9]([O:11]CC)=O)=[CH:4][CH:3]=1.[Br:16][C:17]1[CH:18]=[CH:19][C:20]([NH:23][NH2:24])=[N:21][CH:22]=1.CCN(C(C)C)C(C)C>CO>[Br:16][C:17]1[CH:18]=[CH:19][C:20]([NH:23][NH:24][C:9](=[O:11])[C:8]([C:5]2[N:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=2)([F:14])[F:15])=[N:21][CH:22]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 115356995-Bromo-2-hydrazinopyridineHCID 46941483Ethyl 2-(6-chloropyridazin-3-yl)-2,2-difluoroacetate

생성물 1

HCID 59233291N'-(5-bromopyridin-2-yl)-2-(6-chloropyridazin-3-yl)-2,2-difluoroacetohydrazide수율 77%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of ethyl 2-(6-chloropyridazin-3-yl)-2,2-difluoroacetate (10.8 g, 45.6 mmol) and 5-bromo-2-hydrazinylpyridine (8.58 g, 45.6 mmol) in anhydrous MeOH (100 mL) was added DIEA (5.90 g, 45.6 mmol). The reaction was stirred at ambient temperature for 18 hrs. The solvent was removed via rotary evaporation and the resulting material was reconstituted in EtOAc. The organic phase was washed with water and concentrated to dryness. The resulting residue was purified by MPLC (EtOAc) to provide the title compound, N′-(5-bromopyridin-2-yl)-2-(6-chloropyridazin-3-yl)-2,2-difluoroacetohydrazide 45E (13.3 g, 35.1 mmol, 77% yield). 1H NMR (400 MHz, CDCl3) δ ppm 6.62 (d, J=8.84 Hz, 1 H) 7.11 (d, J=9.35 Hz, 1 H) 7.47-7.60 (m, 2 H) 8.06 (d, J=2.53 Hz, 1 H). ESI-MS:m/z 377.9 (M+H)+.

후처리

  1. customThe solvent was removed via rotary evaporation
  2. washThe organic phase was washed with water
  3. concentrationconcentrated to dryness
  4. customThe resulting residue was purified by MPLC (EtOAc)

출처 및 근거

ORD 기록
ord-7debc1cd7ee945158af263b135947272
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178534B2

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