Trifluoroacetic acid → 3-(1-(4-aminophenyl)-1H-1,2,3-triazol-4-yl)-5-(4-(ethylsulfonyl)piperazin-1-yl)pyrazin-2-amine
Reaktionsgleichung
C(OC([N:8]([C:16]1[C:21]([C:22]2[N:23]=[N:24][N:25]([C:27]3[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=3)[CH:26]=2)=[N:20][C:19]([N:34]2[CH2:39][CH2:38][N:37]([S:40]([CH2:43][CH3:44])(=[O:42])=[O:41])[CH2:36][CH2:35]2)=[CH:18][N:17]=1)C(=O)OC(C)(C)C)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:33][C:30]1[CH:29]=[CH:28][C:27]([N:25]2[CH:26]=[C:22]([C:21]3[C:16]([NH2:8])=[N:17][CH:18]=[C:19]([N:34]4[CH2:39][CH2:38][N:37]([S:40]([CH2:43][CH3:44])(=[O:42])=[O:41])[CH2:36][CH2:35]4)[N:20]=3)[N:23]=[N:24]2)=[CH:32][CH:31]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Tert-butyl N-tert-butoxycarbonyl-3-(1-(4-aminophenyl)-1H-1,2,3-triazol-4-yl)-5-(4-(ethylsulfonyl)piperazin-1-yl)pyrazin-2-ylcarbamate (64 mg, 0.1016 mmol) was dissolved in DCM (5 mL) and treated with TFA (500 μL, 6.490 mmol). The reaction was allowed to stir at ambient temperature overnight and then the solvent removed in vacuo. The resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected and freeze-dried to give the title compound (24.3 mg, 30% Yield). 1H NMR (400.0 MHz, DMSO) d 1.24 (t, J=7.4 Hz, 3H), 3.11 (q, J=7.4 Hz, 2H), 3.30-3.33 (m, 4H), 3.50-3.52 (m, 4H), 6.77 (d, J=8.6 Hz, 2H), 7.67 (d, J=8.8 Hz, 2H), 7.88 (s, 1H) and 9.09 (s, 1H) ppm; MS (ES+) 430.0