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2,2,4-Trimethyl-1,2-dihydro-6-quinolinol → 4-(2,2,4-Trimethyl-1,2-dihydroquinolin-6-yloxy)quinazoline

HRID 454028
Notes
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Reaction equation

HRID 454028 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8](OCC3CCN(C)CC3)=[C:9](OC)[CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH3:23][C:24]1([CH3:36])[CH:33]=[C:32]([CH3:34])[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([OH:35])[CH:30]=2)[NH:25]1>>[CH3:23][C:24]1([CH3:36])[CH:33]=[C:32]([CH3:34])[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([O:35][C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]=[CH:4][N:3]=3)[CH:30]=2)[NH:25]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 5997992,2,4-Trimethyl-1,2-dihydro-6-quinolinolHCID 117822304-Chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline

Product 1

HCID 866024354-(2,2,4-Trimethyl-1,2-dihydroquinolin-6-yloxy)quinazolineYield 110.3%

Procedure

Using a procedure analogous to that described for Example 9, 4-chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline (0.13 g, 0.4 mmol), (prepared as described for the starting material in Example 10), was reacted with 2,2,4-trimethyl-1,2-dihydroquinolin-6-ol (95 mg, 0.5 mmol), (IZV. ACAD. NAVK. SSSR. Ser. Khim. 1981, 9, 2008), to give 6-methoxy-74(1-methylpiperidin-4-yl)methoxy)-4-(2,2,4-trimethyl-1,2-dihydroquinolin-6-yloxy)quinazoline (140 mg, 74%).

Workup

  • custom(prepared
  • Sources & evidence

    ORD record
    ord-217caefd62704e71b074ff2261321d31
    Source dataset
    uspto-grants-2013_07
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US08492560B2

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes