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Sodium Bicarbonate → 3-methyl-7-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinoxalin-2(1H)-one

HRID 219264
ノート
印刷プレビュー

反応式

HRID 219264 の反応式
[CH3:1][C:2]1[C:11](=[O:12])[NH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:13][C:14](OC(C)(C)C)=O)[CH:8]=2)[N:3]=1.CC1C(=O)NC2C(N=1)=CC(CC(OC(C)(C)C)=O)=CC=2.[C:41]1([C:47]2[N:52]=[N:51][C:50]([NH:53][NH2:54])=[CH:49][CH:48]=2)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>O1CCOCC1.CCOC(C)=O>[CH3:1][C:2]1[C:11](=[O:12])[NH:10][C:9]2[C:4]([N:3]=1)=[CH:5][CH:6]=[C:7]([CH2:13][C:14]1[N:51]3[N:52]=[C:47]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[CH:48]=[CH:49][C:50]3=[N:53][N:54]=1)[CH:8]=2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 64098423-Hydrazinyl-6-phenylpyridazineHCID 67503359HCID 67503359、化合物HCID 67503364Tert-butyl 2-(2-methyl-3-oxo-3,4-dihydroquinoxalin-6-yl)acetate

生成物 1

HCID 67502411
3-methyl-7-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinoxalin-2(1H)-one

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
150 °C

実験手順

A mixture of tert-butyl 2-(2-methyl-3-oxo-3,4-dihydroquinoxalin-6-yl)acetate (0.10 g, 0.36 mmol), tert-butyl 2-(3-methyl-2-oxo-1,2-dihydroquinoxalin-6-yl)acetate (0.10 g, 0.36 mmol), 1-(6-phenylpyridazin-3-yl)hydrazine (0.081 g, 0.44 mmol) and p-toluenesulfonic acid monohydrate (0.069 g, 0.36 mmol) in 3 mL of dioxane was heated with microwave at 150° C. for 1 hour. The mixture was diluted with 70 mL of EtOAc and 40 mL of satd. NaHCO3 solution. The organic phase was separated and was washed with 40 mL of brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by prep-HPLC to resolve the regiostereomers as example compounds 494 and 495. For each regiosteroemer MS (ESI pos. ion) m/z: 369 (MH+). Calc'd exact mass for C21H16N6O: 368.

後処理

  1. customThe organic phase was separated
  2. washwas washed with 40 mL of brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by prep-HPLC

出典と根拠

ORDレコード
ord-9d901978b5c243a2b3199d2ac709a6bd
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08198448B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート