Trifluoroacetic acid → HCID 135510683, compound

HRID 1826308Notes

Reaction equation

HRID 1826308 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-e277b97e1de548b2aef6b8f83d2ff7ca
Source dataset
uspto-grants-2006_05
Patent number
US07049438B2

Reaction notes

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