HCID 21936072, compound → HCID 135594114, compound

HRID 1241571Notes

Reaction equation

HRID 1241571 reaction equation
Cl.Cl.C([O:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15]([NH:21][C:22]3[C:27]([Cl:28])=[CH:26][CH:25]=[C:24]4[O:29][CH2:30][O:31][C:23]=34)=[N:16][CH:17]=[N:18]2)=[CH:13][C:12]=1[O:32][CH3:33])C1C=CC=CC=1>FC(F)(F)C(O)=O>[Cl:28][C:27]1[C:22]([NH:21][C:15]2[C:14]3[C:19](=[CH:20][C:11]([OH:10])=[C:12]([O:32][CH3:33])[CH:13]=3)[N:18]=[CH:17][N:16]=2)=[C:23]2[O:31][CH2:30][O:29][C:24]2=[CH:25][CH:26]=1

Participants

3

Reactant 1

HCID 21936072HCID 21936072, compound

Product 1

HCID 135594114HCID 135594114, compoundYield 111.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 7-benzyloxy-4-(6-chloro-2,3-methylenedioxyanilino)-6-methoxyquinazoline dihydrochloride (3.3 g) and trifluoroacetic acid (60 ml) was heated to reflux for 4 hours. The mixture was evaporated. The residue was diluted with water and methanol and the mixture was basified to pH 7.5 by the addition of a saturated aqueous sodium carbonate solution. The methanol was evaporated and the resultant solid was isolated and washed with water. There was thus obtained the title compound as a solid (2.5 g); NMR Spectrum: (DMSOd6 and CF3CO2D) 3.95 (s, 3H), 6.1 (s, 2H), 6.95 (d, 1H), 7.1 (m, 2H), 8.1 (s, 1H), 8.4 (s, 1H), 9.85 (br s, 1H), 10.7 (br s, 1H); Mass Spectrum: M+H+ 346 and 348.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hours
  3. customThe mixture was evaporated
  4. additionThe residue was diluted with water and methanol
  5. additionthe mixture was basified to pH 7.5 by the addition of a saturated aqueous sodium carbonate solution
  6. customThe methanol was evaporated
  7. customthe resultant solid was isolated
  8. washwashed with water

Sources & evidence

ORD record
ord-873363f2dcd24d758bde56baae8ed525
Source dataset
uspto-grants-2006_10
Patent number
US07115615B2

Reaction notes

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