Trifluoroacetic acid → HCID 68328601, compound
Reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[C:11]([C:13]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([C:22]5[S:23][CH:24]=[N:25][N:26]=5)[CH:20]=4)[N:15](C(OC(C)(C)C)=O)[CH:14]=3)[CH:10]=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[S:23]1[CH:24]=[N:25][N:26]=[C:22]1[C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[C:11]1[N:12]=[C:7]([N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[CH:8]=[CH:9][CH:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of tert-butyl 3-(6-morpholinopyridin-2-yl)-5-(1,3,4-thiadiazol-2-yl)-1H-indole-1-carboxylate (86.0 mg, 0.186 mmol) in DCM (1.0 mL) was added TFA (1.0 mL) and the reaction was stirred at RT for 1 h, then solvent was removed. The residue was diluted with DCM (60 mL) and washed with sat. NaHCO3, dried, filtered and concentrated. The residue was purified with RP-HPLC to give 4-(6-(5-(1,3,4-thiadiazol-2-yl)-1H-indol-3-yl)pyridin-2-yl)morpholine (34.0 mg, 0.094 mmol, 50.4%) as a yellow solid. MS (ESI, pos. ion) m/z: 364 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.78 (1H, br. s.), 9.52 (1H, s), 9.17 (1H, d, J=1.4 Hz), 8.16 (1H, d, J=2.5 Hz), 7.92 (1H, dd, J=8.6, 1.6 Hz), 7.53-7.65 (2H, m), 7.24 (1H, d, J=7.6 Hz), 6.66 (1H, d, J=8.4 Hz), 3.78-3.90 (4H, m), 3.57-3.69 (4H, m).