Phosphorus oxychloride → HCID 59233259, 화합물

HRID 1925137노트

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HRID 1925137 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:10](=O)[C:11]([C:14]2[N:15]=[N:16][C:17]([Cl:20])=[CH:18][CH:19]=2)([F:13])[F:12])=[N:6][CH:7]=1.P(Cl)(Cl)(Cl)(Cl)Cl.O=P(Cl)(Cl)Cl>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([C:11]([C:14]3[N:15]=[N:16][C:17]([Cl:20])=[CH:18][CH:19]=3)([F:13])[F:12])=[N:9][N:8]=2)[CH:7]=1

참가 물질

4

반응물 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 59233291N'-(5-bromopyridin-2-yl)-2-(6-chloropyridazin-3-yl)-2,2-difluoroacetohydrazide

생성물 1

HCID 59233259HCID 59233259, 화합물수율 84%

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온도
140 °C

실험 절차

A mixture of N′-(5-bromopyridin-2-yl)-2-(6-chloropyridazin-3-yl)-2,2-difluoroacetohydrazide (1.0 g, 2.64 mmol) and PCl5 (1.2 g, 8 mmol) in POCl3 (40.5 g, 264 mmol) was heated at 140° C. in a sealed tube for 18 hrs. Solvent was removed via rotary evaporation, and the resulting residue was reconstituted in EtOAc. The organic solution was washed with saturated NaHCO3, dried with MgSO4, filtered, and concentrated to dryness. The resulting material was purified via MPLC (Hex:EtOAc, 50-100% gradient) to provide the title compound, 6-bromo-3-((6-chloropyridazin-3-yl)difluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine 45F (0.8 g, 2.21 mmol, 84%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.75 (dd, J=9.85, 1.77 Hz, 1 H) 8.01 (dd, J=9.85, 1.01 Hz, 1 H) 8.31 (d, J=9.09 Hz, 1 H) 8.42-8.51 (m, 1 H) 8.93 (s, 1 H). ESI-MS:m/z 359.9 (M+H)+.

후처리

  1. customSolvent was removed via rotary evaporation
  2. washThe organic solution was washed with saturated NaHCO3
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe resulting material was purified via MPLC (Hex:EtOAc, 50-100% gradient)

출처 및 근거

ORD 기록
ord-1b360e952c4746729feba85fba6764cc
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178534B2

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