Methyl 3-Bromopyruvate → HCID 59233216、化合物

HRID 1925140

反応式

HRID 1925140 の反応式
[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

参加物

5

反応物 3

HCID 352524Methyl 3-BromopyruvateHCID 516892Sodium BicarbonateHCID 59233207HCID 59233207、化合物

生成物 1

HCID 59233216HCID 59233216、化合物

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-8969949d90cd41ceb02c5d5572e19037
出典データセット
uspto-grants-2012_05
特許番号
US08178534B2

関連ノート

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