4-(1-Pyrimidin-2-ylpiperidin-4-ylamino)benzoic acid tert-butyl ester → 4-(1-Pyrimidin-2-ylpiperidin-4-ylamino)benzoic acid
Reaction equation
C([O:5][C:6](=[O:26])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[N:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[CH2:16][CH2:15]2)=[CH:9][CH:8]=1)(C)(C)C>Cl>[N:21]1[CH:22]=[CH:23][CH:24]=[N:25][C:20]=1[N:17]1[CH2:16][CH2:15][CH:14]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([C:6]([OH:26])=[O:5])=[CH:8][CH:9]=2)[CH2:19][CH2:18]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of (11) (0.009 g, 0.025 mmol) in HCl (5 mL, 4M in 1,4-dioxane) was capped with a drying tube and stirred at 25° C. for 12 h. The reaction mixture was evaporated to a pale yellow oily residue (0.009 g, quantitative yield); 1H NMR (DMSO) δ 8.42 (d, 2H, J=4.8), 7.67 (d, 2H, J=8.7), 6.70 (t, 1H, J=4.8), 6.67 (d, 2H, J=9.3), 4.54 (d, 2H, J=13.2), 3.72 (m, 1H), 3.20 (t, 2H, J=11.1), 1.98 (d, 2H, J=10.7), 1.34 (m, 2H); 13C NMR (CDCl3) δ 167.4, 158.9, 157.7, 151.0, 131.2, 117.4, 111.7, 109.7, 48.9, 43.6, 30.9; HRMS (FAB) m/z 299.1518 (M+H)+ (C16H18N4O2 requires 299.1508).
Sources & evidence
- ORD record
- ord-c7b73937b2514214a6365dc2cdd2562d
- Source dataset
- uspto-grants-2000_12
- Patent number
- US06156758
Reaction notes
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