HCID 68328327, compound → HCID 68328329, compound
Reaction equation
[NH2:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[N:12](C(OC(C)(C)C)=O)[CH:11]=[C:10]3[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[N:24]=2)=[N:4][N:3]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[O:32]1[CH2:31][CH2:30][N:29]([C:25]2[N:24]=[C:23]([C:10]3[C:9]4[C:13](=[CH:14][CH:15]=[C:7]([C:5]5[S:6][C:2]([NH2:1])=[N:3][N:4]=5)[CH:8]=4)[NH:12][CH:11]=3)[CH:28]=[CH:27][CH:26]=2)[CH2:34][CH2:33]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of tert-butyl 5-(5-amino-1,3,4-thiadiazol-2-yl)-3-(6-morpholinopyridin-2-yl)-1H-indole-1-carboxylate (212 mg, 0.443 mmol) in DCM/TFA (1:1, 4 mL) was stirred at RT for 1 h, then the solvent was removed. The residue was diluted with DCM and washed with sat. NaHCO3. The organic layer was dried, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 0.5-4.5% MeOH in DCM) to give 5-(3-(6-morpholinopyridin-2-yl)-1H-indol-5-yl)-1,3,4-thiadiazol-2-amine (38.0 mg, 0.100 mmol, 22.7%) as a light brown solid. MS (ESI, pos. ion) m/z: 379 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 11.67 (1H, d, J=2.2 Hz), 8.82 (1H, d, J=1.6 Hz), 8.11 (1H, d, J=2.5 Hz), 7.74 (1H, dd, J=8.6, 1.8 Hz), 7.53-7.62 (1H, m), 7.48 (1H, d, J=8.6 Hz), 7.30 (1H, s), 7.22 (1H, d, J=7.4 Hz), 6.64 (1H, d, J=8.4 Hz), 3.79-3.93 (4H, m), 3.55-3.67 (4H, m).