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

HRID 40241

반응식

HRID 40241 반응식
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][C:13](O)=O)[CH:10]=2)[N:5]=[CH:4][NH:3]1.[C:16]1([C:22]2[N:27]=[N:26][C:25]([NH:28][NH2:29])=[CH:24][CH:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>O1CCOCC1.CCOC(C)=O>[C:16]1([C:22]2[CH:23]=[CH:24][C:25]3[N:26]([C:13]([CH2:12][C:9]4[CH:10]=[C:11]5[C:6](=[CH:7][CH:8]=4)[N:5]=[CH:4][NH:3][C:2]5=[O:1])=[N:29][N:28]=3)[N:27]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

7

반응물 4

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 64098423-Hydrazinyl-6-phenylpyridazineHCID 1360264712-(4-Oxo-3,4-dihydroquinazolin-6-yl)acetic acid

생성물 1

HCID 1359874736-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinazolin-4(3H)-one

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

반응 조건

온도
150 °C

실험 절차

A mixture of 2-(4-oxo-3,4-dihydroquinazolin-6-yl)acetic acid (0.10 g, 0.5 mmol), 1-(6-phenylpyridazin-3-yl)hydrazine (0.1 g, 0.6 mmol) and p-toluenesulfonic acid monohydrate (0.09 g, 0.5 mmol) in 3 mL of dioxane was heated with microwave at 150° C. for 1 hour in a microwave tube. 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 a silica gel column chromatography (EtOAc to 15% MeOH/EtOAc) to give light yellow solid as desired product 6-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinazolin-4(3H)-one. MS (ESI, pos. ion) m/z: 355.1 (M+1).

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 a silica gel column chromatography (EtOAc to 15% MeOH/EtOAc)

출처 및 근거

ORD 기록
ord-0a32eec8b9eb4426b5067b6befb1011a
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524900B2

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