Trifluoroacetic acid → HCID 67415388, compound

HRID 2099370Notes

Reaction equation

HRID 2099370 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:25][CH:26]3[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]3)=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]=[CH:15][N:14]=1>C(Cl)Cl.C([SiH](CC)CC)C>[ClH:8].[ClH:8].[Cl:8][C:9]1[C:10]([F:42])=[C:11]([NH:12][C:13]2[C:22]3[C:17](=[CH:18][C:19]([O:25][CH:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)=[C:20]([O:23][CH3:24])[CH:21]=3)[N:16]=[CH:15][N:14]=2)[CH:39]=[CH:40][CH:41]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67415632HCID 67415632, compound

Product 1

HCID 67415388HCID 67415388, compoundYield 317.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 12052TriethylsilaneSolvent

Procedure

Trifluoroacetic acid (50 ml) was added to a solution of tert-butyl 4-({4-[3-chloro-2-fluoroanilino]-6-methoxyquinazolin-7-yl}oxy)piperidine-1-carboxylate (750 mg, 1.49 mmol) in methylene chloride (1 ml) and triethylsilane (1 ml) and the solution stirred for 1 hour. The reaction mixture was then evaporated under reduced pressure and the residues re-dissolved in EtOAc (5 ml). This solution was then treated with 1M HCl/diethylether (1 ml) followed by more diethylether (50 ml) to give a white precipitate. The resulting solids were collected following centrifugation and dried under vacuum to give N-(3-chloro-2-fluorophenyl)-6-methoxy-7-(piperidin-4-yloxy)quinazolin-4-amine dihydrochloride as a white solid (750 mg); 1H NMR Spectrum: (DMSO-d6): 2.00-2.20 (m, 2H), 2.25-2.45 (m, 2H), 3.15-3.50 (m, 4H), 4.15 (s, 3H), 5.02 (m, 1H), 7.48 (m, 1H), 7.60-7.85 m, 3H), 8.35 (s, 1H), 8.85 (s, 1H), 9.56 (bs, 2H); Mass Spectrum: (M+H)+ 403.

Workup

  1. customThe reaction mixture was then evaporated under reduced pressure
  2. dissolutionthe residues re-dissolved in EtOAc (5 ml)
  3. additionThis solution was then treated with 1M HCl/diethylether (1 ml)
  4. customto give a white precipitate
  5. customThe resulting solids were collected
  6. customdried under vacuum

Sources & evidence

ORD record
ord-7e24ec41221b4e199e02cd6411153a38
Source dataset
uspto-grants-2009_08
Patent number
US07569577B2

Reaction notes

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