Trifluoroacetic acid → HCID 22140767, compound

HRID 641758Notes

Reaction equation

HRID 641758 reaction equation
[Cl:1][C:2]1[CH:42]=[C:41]([Cl:43])[C:40]([O:44][CH3:45])=[CH:39][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:22][CH2:23][CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH:27]3C(OC(C)(C)C)=O)=[CH:12][C:13]=2[O:15][CH:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[N:8]=[CH:7][N:6]=1.FC(F)(F)C(O)=O>>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:42]=[C:41]([Cl:43])[C:40]([O:44][CH3:45])=[CH:39][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:22][CH2:23][CH2:24][CH2:25][N:26]3[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]3)=[CH:12][C:13]=2[O:15][CH:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[N:8]=[CH:7][N:6]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68577983HCID 68577983, compound

Product 1

HCID 22140767HCID 22140767, compoundYield 292%

Procedure

A mixture of 4-(2,4-dichloro-5-methoxyanilino)-7-[3-(tert-butoxycarbonylpiperazin-1-yl)propoxy]-5-tetrahydropyran-4-yloxyquinazoline (0.12 g) and trifluoroacetic acid (2 ml) was stirred at ambient temperature for 2 hours. The mixture was evaporated and the residue was triturated under diethyl ether. The resultant solid was isolated and dried under vacuum. The solid was dissolved in diethyl ether and 6M hydrogen chloride gas in diethyl ether (0.5 ml) was added. The resultant solid was isolated, washed with diethyl ether and dried under vacuum. There was thus obtained the title compound (0.112 g); NMR Spectrum: (DMSOd6 and CF3CO2H) 1.9-2.1 (m, 2H), 2.15 (d, 2H), 2.28-2.4 (m, 2H), 3.4 (m, 2H), 3.4-3.9 (m, 10H), 3.92 (s, 3H), 3.95 (m, 2H), 4.39 (t, 2H), 5.2 (m, 1H), 7.0 (d, 1H), 7.2 (d, 1H), 7.78 (s, 1H), 7.82 (s, 1H), 8.9 (s, 1H); Mass Spectrum: M+H+ 562 and 564.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was triturated under diethyl ether
  3. customThe resultant solid was isolated
  4. customdried under vacuum
  5. dissolutionThe solid was dissolved in diethyl ether
  6. addition6M hydrogen chloride gas in diethyl ether (0.5 ml) was added
  7. customThe resultant solid was isolated
  8. washwashed with diethyl ether
  9. customdried under vacuum

Sources & evidence

ORD record
ord-af1bd6d649f348558569fb4204410dfe
Source dataset
uspto-grants-2010_04
Patent number
US07696214B2

Reaction notes

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