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tert-Butyl 4-[(4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxyquinazolin-7-yloxy)methyl]piperidine-1-carboxylate → 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-(piperidin-4-ylmethoxy)quinazoline

HRID 2068061
Notes
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Reaction equation

HRID 2068061 reaction equation
[F:1][C:2]1[C:10]([O:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:24][CH2:25][CH:26]4[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]4)=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[CH:14][N:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:39])[NH:6]2>Cl.O1CCOCC1>[F:1][C:2]1[C:10]([O:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:24][CH2:25][CH:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[CH:14][N:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:39])[NH:6]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 67019228tert-Butyl 4-[(4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxyquinazolin-7-yloxy)methyl]piperidine-1-carboxylate

Product 1

HCID 589602204-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-(piperidin-4-ylmethoxy)quinazolineYield 86.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 4-[(4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxyquinazolin-7-yloxy)methyl]piperidine-1-carboxylate [285 mg (containing 13.5% triphenylphospine oxide), 0.49 mmol] was dissolved in 4M hydrogen chloride in dioxane (5 ml) and stirred at ambient temperature for 3 hours. The solvent was removed under reduced pressure and the solid suspended in methylene chloride and filtered off. The solid was dissolved in methanol and absorbed onto an Isolute SCX column which was washed through with methanol and then the product eluted with 7N ammonia in methanol. Concentration of the fractions gave 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-(piperidin-4-ylmethoxy)quinazoline (185 mg, 86%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. filtrationfiltered off
  3. dissolutionThe solid was dissolved in methanol
  4. customabsorbed onto an Isolute SCX column which
  5. washwas washed through with methanol
  6. washthe product eluted with 7N ammonia in methanol

Sources & evidence

ORD record
ord-c355aecf9289455ab6e67d27098f422a
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08293902B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes