Trifluoroacetic acid → HCID 136104957, compound
Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:17]=[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([NH:24]C(=O)OC(C)(C)C)[CH2:20][CH2:19]2)[C:15]2[C:10](=[CH:11][C:12]([CH3:32])=[CH:13][CH:14]=2)[N:9]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:24][CH:21]1[CH2:22][CH2:23][N:18]([C:16]2[C:15]3[C:10](=[CH:11][C:12]([CH3:32])=[CH:13][CH:14]=3)[N:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[OH:1])[N:17]=2)[CH2:19][CH2:20]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
tert-Butyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-4-ylcarbamate (3.21 g, 7.39 mmol) was dissolved in CH2Cl2 (55 ml). TFA (50 ml) was added and the reaction was stirred for 1 hour. After evaporating the solvents in vacuo, the crude material was diluted with CH2Cl2 and neutralized with a 1 N NaOH solution. The layers were separated, and the aqueous layer was extracted three times with CH2Cl2 (30 ml). The combined organic layers were dried over MgSO4, filtered, and concentrated to give 2-(4-(4-aminopiperidin-1-yl)-7-methylquinazolin-2-yl)phenol as a yellow solid (2.06 g, 83%). LC/MS: m/z 335.3 (M+H)+ at 1.42 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).