4-[1-(6,7-Dimethoxy-4-p-tolylaminoquinazolin-2-yl)piperidin-4-ylamino]benzoic acid tert-butyl ester → 4-[1-(6,7-Dimethoxy-4-p-tolylaminoquinazolin-2-yl)piperidin-4-ylamino]benzoic acid
Reaction equation
C([O:5][C:6](=[O:42])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[N:29]=[C:28]([NH:30][C:31]4[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=4)[C:27]4[C:22](=[CH:23][C:24]([O:40][CH3:41])=[C:25]([O:38][CH3:39])[CH:26]=4)[N:21]=3)[CH2:16][CH2:15]2)=[CH:9][CH:8]=1)(C)(C)C>FC(F)(F)C(O)=O>[CH3:39][O:38][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][C:24]=1[O:40][CH3:41])[N:21]=[C:20]([N:17]1[CH2:18][CH2:19][CH:14]([NH:13][C:10]3[CH:11]=[CH:12][C:7]([C:6]([OH:42])=[O:5])=[CH:8][CH:9]=3)[CH2:15][CH2:16]1)[N:29]=[C:28]2[NH:30][C:31]1[CH:32]=[CH:33][C:34]([CH3:37])=[CH:35][CH:36]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of (16) (0.040 g, 0.07 mmol) in trifluoroacetic acid (5 mL) was capped with a drying tube and stirred at 25° C. for 12 h. The reaction mixture was evaporated to a light brown solid residue (0.05 g, quantitative yield); 1H NMR (DMSO) δ 12.10 (br s, 1H), 10.56 (br s, 1H), 7.92 (s, 1H) 7.67 (d, 2H, J=8.5), 7.51 (d, 2H, J=8.3), 7.27 (s, 1H), 7.26 (d, 2H, J=7.9), 6.64 (d, 2H, J=8.4), 4.32 (d, 2H, J=12.6), 3.91 (s, 3H), 3.89 (s, 3H), 3.68 (m, 1H), 3.36 (t, 2H, J=10.7), 2.32 (s, 3H), 2.05 (d, 2H, J=8.0), 1.47 (m, 2H); 13C NMR (DMSO) δ 167.4, 157.2, 155.4, 151.4, 150.7, 147.0, 136.4, 135.0, 134.6, 131.2, 129.1, 124.0, 117.0, 111.2, 104.3, 102.2, 99.1, 56.3, 56.1, 47.9, 43.5, 30.8, 20.6; HRMS (FAB) m/z 514.2459 M+H)+ (C29H31N5O4 requires 514.2454); Anal. (C29H31N5O4 ·1CF3COOH·11/4H2O) C, H, N.
Sources & evidence
- ORD record
- ord-9f850714019d494da008ecaf8a5d6062
- Source dataset
- uspto-grants-2000_12
- Patent number
- US06156758
Reaction notes
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