Trifluoroacetic acid → 5-(5-Phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)pyridine-3-sulfonamide
Reaktionsgleichung
C([NH:5][S:6]([C:9]1[CH:10]=[N:11][CH:12]=[C:13]([C:15]2[C:24]3[C:19](=[C:20]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:21]=[CH:22][CH:23]=3)[C:18]([NH:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=3)=[N:17][N:16]=2)[CH:14]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>>[C:25]1([C:20]2[CH:21]=[CH:22][CH:23]=[C:24]3[C:19]=2[C:18]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)=[N:17][N:16]=[C:15]3[C:13]2[CH:14]=[C:9]([S:6]([NH2:5])(=[O:7])=[O:8])[CH:10]=[N:11][CH:12]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1Komponenten
3
Versuchsvorschrift
N-(tert-Butyl)-5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)pyridine-3-sulfonamide (0.0300 g, 0.0570 mmol) was dissolved in TFA (5.00 mL, 64.9 mmol) and stirred at room temperature for 12 h. TFA was removed under reduced pressure and reaction mixture was diluted with saturated NaHCO3 (50 mL). The reaction mixture was extracted with EtOAc (3×30 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by preparative HPLC (Condition 16 as described in general methods) to afford 5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)pyridine-3-sulfonamide (10.0 mg, 37.3%) as a white solid. LCMS (Condition 4): retention time 2.25 min, [M+1]=469.2. HPLC (Condition 28): retention time=5.73 min, purity 99.07%. 1H NMR (400 MHz, CD3OD) δ 4.68 (s, 2 H), 7.24 (dd, J=4.8 Hz, J=7.6 Hz, 1 H), 7.27 (d, J=7.6 Hz, 1 H), 7.52 (br s, 5 H), 7.71-7.77 (m, 2 H), 7.88 (dd, J=1.6 Hz, J=8.4 Hz, 1 H), 7.95 (dd, J=7.2 Hz, J=8.4 Hz, 1 H), 8.30-8.31 (m, 1 H), 8.57 (dd, J=2.0 Hz, J=2.4 Hz, 1 H), 9.07 (d, J=2.0 Hz, 1 H), 9.21 (d, J=2.4 Hz, 1 H).