Trifluoroacetic acid → HCID 135830908, compound

HRID 641750Notes

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-benzyloxy-4-(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-2ee109c9477a4e059474dbcc2179581b
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696214B2

Reaction notes

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