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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 40389
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HRID 40389 반응식
[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
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참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
150 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9dd956c324774b6395452e42afc276c7
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08524900B2

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