Trifluoroacetic acid → HCID 21935994, compound

HRID 1371481Notes

Reaction equation

HRID 1371481 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:27]=[C:26]3[C:21]([C:22]([NH:28][C:29]4[C:34]([Cl:35])=[CH:33][CH:32]=[C:31]5[O:36][CH2:37][O:38][C:30]=45)=[N:23][CH:24]=[N:25]3)=[CH:20][C:19]=2[O:39][CH3:40])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[ClH:35].[ClH:35].[Cl:35][C:34]1[C:29]([NH:28][C:22]2[C:21]3[C:26](=[CH:27][C:18]([O:17][CH2:16][CH2:15][CH2:14][N:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)=[C:19]([O:39][CH3:40])[CH:20]=3)[N:25]=[CH:24][N:23]=2)=[C:30]2[O:38][CH2:37][O:36][C:31]2=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21936006HCID 21936006, compound

Product 1

HCID 21935994HCID 21935994, compoundYield 225.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 7-[3-(4-tert-butoxycarbonylpiperazin-1-yl)propoxy]-4-(6-chloro-2,3-methylenedioxyanilino)-6-methoxyquinazoline (0.286 g), trifluoroacetic acid (0.5 ml) and methylene chloride (6 ml) was stirred at ambient temperature for 3 hours. The solvent was evaporated and the residue was partitioned between methylene chloride and a saturated aqueous sodium bicarbonate solution. The organic phase was washed with water and with brine, dried over magnesium sulphate and evaporated. The material so obtained was triturated under a 6M solution of hydrogen chloride in diethyl ether. There was thus obtained the title compound (0.205 g); NMR Spectrum: (DMSOd6 and CF3CO2D) 2.35 (m, 2H), 3.2–3.9 (m, 10H), 4.0 (s, 3H), 4.35 (m, 2H), 6.12 (s, 2H), 7.0 (s, 1H), 7.1 (s, 1H), 7.38 (s, 1H), 8.15 (s, 1H), 8.85 (s, 1H); Mass Spectrum: M+H+ 472 and 474

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between methylene chloride
  3. washThe organic phase was washed with water and with brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe material so obtained
  7. customwas triturated under a 6M solution of hydrogen chloride in diethyl ether

Sources & evidence

ORD record
ord-bd2696c32872435a96044179f5ca9961
Source dataset
uspto-grants-2007_01
Patent number
US07157467B2

Reaction notes

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