Trifluoroacetic acid → N-(5-(4-(piperidin-4-yloxy)pyrido[3,2-d]pyrimidin-6-yl)pyridin-3-yl)benzenesulfonamide
Reaction equation
[C:1]1([S:7]([NH:10][C:11]2[CH:12]=[C:13]([C:17]3[CH:18]=[CH:19][C:20]4[N:21]=[CH:22][N:23]=[C:24]([O:27][CH:28]5[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]5)[C:25]=4[N:26]=3)[CH:14]=[N:15][CH:16]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:31]1[CH2:32][CH2:33][CH:28]([O:27][C:24]2[C:25]3[N:26]=[C:17]([C:13]4[CH:12]=[C:11]([NH:10][S:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)(=[O:8])=[O:9])[CH:16]=[N:15][CH:14]=4)[CH:18]=[CH:19][C:20]=3[N:21]=[CH:22][N:23]=2)[CH2:29][CH2:30]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of tert-butyl 4-(6-(5-(phenylsulfonamido)-pyridine-3-yl)pyrido[3,2-d]pyrimidin-4-yloxy)piperidine-1-carboxylate (0.15 g, 0.267 mmol) in DCM (1.333 ml) was added TFA (0.205 ml, 2.67 mmol) at room temperature. After stirring for 30 min at room temperature, the reaction mixture was evaporated in vacuo, to give N-(5-(4-(piperidin-4-yloxy)pyrido[3,2-d]pyrimidin-6-yl)pyridin-3-yl)benzenesulfonamide (0.123 g, 100%) as a yellow oil, which was used in the next step without further purification. 1H-NMR (CDCl3, Varian 400 MHz) δ 1.87-1.92 (2H, m), 2.15-2.22 (2H, m), 2.79-2.85 (2H, m), 3.20-3.24 (2H, m), 5.58-5.62 (1H, m), 7.39-7.42 (3H, m), 7.92-7.94 (2H, m), 8.18-8.20 (2H, m), 8.28 (1H, s), 8.59 (1H, d, J=1.6 Hz), 8.74 (1H, s).
Workup
- customthe reaction mixture was evaporated in vacuo
Sources & evidence
- ORD record
- ord-0e2d2f1302a44297ab7fa96b856ddf0a
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09422298B2
Reaction notes
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