Trifluoroacetic acid → 4-(3-Chloro-2-fluoroanilino)-6-(piperidin-3-yloxy)-7-methoxyquinazoline

HRID 1948917

Reaction equation

HRID 1948917 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:10]([F:42])=[C:11]([CH:39]=[CH:40][CH:41]=1)[NH:12][C:13]1[C:22]2[C:17](=[CH:18][C:19]([O:37][CH3:38])=[C:20]([O:23][CH:24]3[CH2:29][CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25]3)[CH:21]=2)[N:16]=[CH:15][N:14]=1>C(Cl)Cl>[Cl:8][C:9]1[C:10]([F:42])=[C:11]([CH:39]=[CH:40][CH:41]=1)[NH:12][C:13]1[C:22]2[C:17](=[CH:18][C:19]([O:37][CH3:38])=[C:20]([O:23][CH:24]3[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]3)[CH:21]=2)[N:16]=[CH:15][N:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 685245814-(3-Chloro-2-fluoroanilino)-6-(1-tert-butoxycarbonylpiperidin-3-yloxy)-7-methoxyquinazoline

Product 1

HCID 104537624-(3-Chloro-2-fluoroanilino)-6-(piperidin-3-yloxy)-7-methoxyquinazolineYield 52.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5 ml) was added to a solution of 4-(3-chloro-2-fluoroanilino)-6-(1-tert-butoxycarbonylpiperidin-3-yloxy)-7-methoxyquinazoline (0.67 g) in methylene chloride (15 ml) and the reaction mixture was stirred at ambient temperature for 1 hour. The reaction mixture was evaporated under vacuum and the residue dissolved in methylene chloride. The methylene chloride solution was washed with a saturated solution of sodium bicarbonate, water, brine, dried over MgSO4 and evaporated to give 4-(3-chloro-2-fluoroanilino)-7-methoxy-6-(piperidin-3-yloxy)quinazoline (0.28 g); Mass Spectrum: (M+H)+ 403.

Workup

  1. customThe reaction mixture was evaporated under vacuum
  2. dissolutionthe residue dissolved in methylene chloride
  3. washThe methylene chloride solution was washed with a saturated solution of sodium bicarbonate, water, brine
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-db4a88da36e54ef591103667bca687ef
Source dataset
uspto-grants-2013_03
Patent number
US08399667B2

Linked notes

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