Trifluoroacetic acid → HCID 135830908, compound

HRID 1826290Notes

Reaction equation

C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:19][C:20]3[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=3[Br:28])=[N:14][CH:15]=[N:16]2)=[C:11]([O:29][CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:10]=1)C1C=CC=CC=1.FC(F)(F)C(O)=O>>[Br:28][C:21]1[CH:22]=[CH:23][C:24]([O:26][CH3:27])=[CH:25][C:20]=1[NH:19][C:13]1[C:12]2[C:17](=[CH:18][C:9]([OH:8])=[CH:10][C:11]=2[O:29][CH:30]2[CH2:31][CH2:32][NH:33][CH2:34][CH2:35]2)[N:16]=[CH:15][N:14]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 10165579HCID 10165579, compound

Product 1

HCID 135830908HCID 135830908, compound

Conditions

Temperature: 80 °C

Procedure

A mixture of 7-benzyloxy4-(2-bromo-5-methoxyanilino)-5-piperidin-4-yloxyquinazoline (0.35 g) and trifluoroacetic acid (6 ml) was stirred and heated to 80° C. for 5 hours. The mixture was evaporated and the residue was dissolved in water (12 ml). The solution was basified to pH8 by the addition of sodium bicarbonate. The resultant precipitate was isolated, washed with water and with ethyl acetate and dried under vacuum. There was thus obtained the title compound (0.26 g); NMR Spectrum: (DMSOd6) 1.95–2.15 (m, 2H), 2.32 (d, 2H), 3.05 (t, 2H), 3.3–3.4 (m, 2H), 3.8 (s, 3H), 5.0 (m, 1H), 6.75 (m, 2H), 6.85 (s, 1H), 7.6 (d, 1H), 7.98 (s, 1H), 8.4 (s, 1H), 9.58 (s, 1H); Mass Spectrum: M+H+ 445 and 447.

Workup

customThe mixture was evaporated
dissolutionthe residue was dissolved in water (12 ml)
additionThe solution was basified to pH8 by the addition of sodium bicarbonate

Sources & evidence

ORD record: ord-2288bed3b27c414f989e3784c926bf4b
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07049438B2

Reaction notes

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