Methyl 3-Bromopyruvate → HCID 59233216, 화합물

HRID 1925140

반응식

HRID 1925140 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([F:20])([F:19])[C:12]3[N:17]=[N:16][C:15]([NH2:18])=[CH:14][CH:13]=3)=[N:9][N:10]=2)[CH:7]=1.Br[CH2:22][C:23](=O)[C:24]([O:26][CH3:27])=[O:25].C([O-])(O)=O.[Na+]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([F:20])([F:19])[C:12]3[CH:13]=[CH:14][C:15]4[N:16]([CH:22]=[C:23]([C:24]([O:26][CH3:27])=[O:25])[N:18]=4)[N:17]=3)=[N:9][N:10]=2)[CH:7]=1

참가 물질

5

반응물 3

HCID 352524Methyl 3-BromopyruvateHCID 516892Sodium BicarbonateHCID 59233207HCID 59233207, 화합물

생성물 1

HCID 59233216HCID 59233216, 화합물

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

A reaction mixture of 6-((6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)difluoromethyl)pyridazin-3-amine (11.0 g, 32.2 mmol), methyl 3-bromo-2-oxopropanoate (11.67 g, 64.5 mmol), and NaHCO3 (10.84 g) in dioxane (150 mL) was heated at 80° C. for 4 hrs to provide a red reaction mixture. Solids were filtered off, rinsed with dioxane, and the combined filtrates were concentrated via rotary evaporation. The resulting residue was dissolved in EtOAc and washed with 0.1 N NaOH until the red color no longer persisted. The organic phase was then separated and concentrated to dryness. The resulting material was purified via MPLC (5:95, MeOH/EtOAc) to provide the title compound, 45I (4.0 g, 9.45 mmol, 30%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.88 (s, 3 H) 7.77 (dd, J=9.73, 1.64 Hz, 1 H) 7.85 (d, J=9.60 Hz, 1 H) 7.97-8.08 (m, 1 H) 8.53 (d, J=9.60 Hz, 1 H) 8.98 (d, J=1.01 Hz, 1 H) 9.02 (s, 1 H). ESI-MS:m/z 423.1 (M+H)+.

후처리

  1. customto provide a red reaction mixture
  2. filtrationSolids were filtered off
  3. washrinsed with dioxane
  4. concentrationthe combined filtrates were concentrated via rotary evaporation
  5. dissolutionThe resulting residue was dissolved in EtOAc
  6. washwashed with 0.1 N NaOH until the red color
  7. customThe organic phase was then separated
  8. concentrationconcentrated to dryness
  9. customThe resulting material was purified via MPLC (5:95, MeOH/EtOAc)

출처 및 근거

ORD 기록
ord-8969949d90cd41ceb02c5d5572e19037
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178534B2

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