Trifluoroacetic acid → HCID 135510683, compound

HRID 641765Notes

Reaction equation

HRID 641765 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)=[C:13]([O:32][CH:33]2[CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35][CH2:34]2)[CH:12]=1)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])=[CH:12][C:13]=3[O:32][CH:33]3[CH2:34][CH2:35][NH:36][CH2:37][CH2:38]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 2

HCID 6422Trifluoroacetic acidHCID 22140816HCID 22140816, compound

Product 1

HCID 135510683HCID 135510683, compoundYield 78.2%

Conditions

Temperature
80 °C

Procedure

A mixture of 7-benzyloxy-5-[N-(tert-butoxycarbonyl)piperidin-4-yloxy]-4-(6-chloro-2,3-methylenedioxyanilino)quinazoline dihydrochloride (2.3 g) and trifluoroacetic acid (28 ml) was stirred and heated to 80° C. for 6 hours. The mixture was evaporated and the residue was dissolved in water and the solution was basified to pH10 by the addition of 1N aqueous sodium hydroxide solution. The mixture was stirred at ambient temperature for 1 hour. The solid was isolated, washed with water and dried under vacuum. There was thus obtained the title compound (1.1 g); NMR Spectrum: (DMSOd6) 1.6-1.8 (m, 2H), 2.0-2.15 (m, 2H), 2.65-2.75 (m, 2H), 2.9-3.05 (m, 2H), 4.8 (m, 1H), 6.1 (s, 2H), 6.62 (s, 1H), 6.7 (s, 1H), 6.92 (d, 1H), 7.05 (d, 1H), 8.25 (s, 1H), 9.2 (s, 1H); Mass Spectrum: M+H+ 415 and 417.

Workup

  1. customThe mixture was evaporated
  2. dissolutionthe residue was dissolved in water
  3. additionthe solution was basified to pH10 by the addition of 1N aqueous sodium hydroxide solution
  4. stirringThe mixture was stirred at ambient temperature for 1 hour
  5. customThe solid was isolated
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-8bb8c819a96f4c3c8b6f137aa3abc7cf
Source dataset
uspto-grants-2010_04
Patent number
US07696214B2

Reaction notes

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