Trifluoroacetic acid → HCID 22591472, compound

HRID 22781Notes

Reaction equation

HRID 22781 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:25]=[C:24]3[C:19]([C:20]([NH:26][C:27]4[C:35]5[O:34][CH:33]=[CH:32][C:31]=5[CH:30]=[CH:29][C:28]=4[Cl:36])=[N:21][CH:22]=[N:23]3)=[CH:18][C:17]=2[O:37][CH3:38])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:36][C:28]1[CH:29]=[CH:30][C:31]2[CH:32]=[CH:33][O:34][C:35]=2[C:27]=1[NH:26][C:20]1[C:19]2[C:24](=[CH:25][C:16]([O:15][CH2:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[C:17]([O:37][CH3:38])[CH:18]=2)[N:23]=[CH:22][N:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22591455HCID 22591455, compound

Product 1

HCID 22591472HCID 22591472, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 7-(N-tert-butoxycarbonylpiperidin-4-ylmethoxy)-4-(6-chlorobenzofuran-7-ylamino)-6-methoxyquinazoline (0.4 g), trifluoroacetic acid (3 ml) and methylene chloride (12 ml) was stirred at ambient temperature for 3 hours. The mixture was evaporated and the residue was diluted with water. The mixture was basified to pH11 by the addition of 1 N aqueous sodium hydroxide solution and methylene chloride was added. The precipitate which was formed was collected by filtration, washed with water and dried under vacuum to give the title compound (0.195 g); NMR Spectrum: (DMSOd6 and CF3CO2D) 1.55 (m, 2H), 2.0 (m, 2H), 2.25 (m, 1H), 2.95 (m, 2H), 3.4 (m, 2H), 4.05 (s, 3H), 4.2 (d, 2H), 7.1 (d, 1H), 7.4 (s, 1H), 7.55 (d, 1H), 7.8 (d, 1H), 8.05 (d, 1H), 8.2 (s, 1H), 8.85 (s, 1H), Mass Spectrum: M−H− 437.

Workup

  1. customThe mixture was evaporated
  2. additionthe residue was diluted with water
  3. additionThe mixture was basified to pH11 by the addition of 1 N aqueous sodium hydroxide solution and methylene chloride
  4. additionwas added
  5. customThe precipitate which was formed
  6. filtrationwas collected by filtration
  7. washwashed with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-4ba40502caba4ec296e1b49588043d09
Source dataset
uspto-grants-2005_02
Patent number
US06849625B2

Reaction notes

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