1-(4-Azidobenzoyl)-3-(pyrrolidin-1-ylmethyl)piperidine → 3-[1-(4-{[3-(pyrrolidin-1-ylmethyl)piperidin-1-yl]carbonyl}phenyl)-1H-1,2,3-triazol-4-yl]-1H-indazole
Reaction equation
[N:1]([C:4]1[CH:23]=[CH:22][C:7]([C:8]([N:10]2[CH2:15][CH2:14][CH2:13][CH:12]([CH2:16][N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:11]2)=[O:9])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[C:24]([C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][N:27]=1)#[CH:25]>C(Cl)Cl>[N:17]1([CH2:16][CH:12]2[CH2:13][CH2:14][CH2:15][N:10]([C:8]([C:7]3[CH:6]=[CH:5][C:4]([N:1]4[CH:25]=[C:24]([C:26]5[C:34]6[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=6)[NH:28][N:27]=5)[N:3]=[N:2]4)=[CH:23][CH:22]=3)=[O:9])[CH2:11]2)[CH2:21][CH2:20][CH2:19][CH2:18]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The title compound was prepared following procedure described for intermediate 10, but starting from 1-(4-azidobenzoyl)-3-(pyrrolidin-1-ylmethyl)piperidine (420 mg; 1.34 mmol; 1.0 eq.) and 3-ethynyl-1H-indazole (190 mg; 1.34 mmol; 1.0 eq.). After purification by preparative HPLC, it was obtained as the formic acid salt. The salt was solubilized in DCM and washed with a saturated solution of NaHCO3 then brine. Organic phase was dried over magnesium sulfate, filtered and concentrated. The resulting oil was suspended in EtOH, and concentrated to dryness to afford the title compound as a yellow powder. 1H NMR (300 Mz, DMSO-d6) δ: 13.37 (s, 1H), 9.37 (s, 1H), 8.36 (d, J=8.1 Hz, 1H), 8.15 (d, J=8.7 Hz, 2H), 7.61 (m, 3H), 7.43 (m, 1H), 7.26 (m, 1H), 4.48 (m, 0.4H), 4.25 (m, 0.6H), 3.70 (m, 0.6H), 3.52 (m, 0.4H), 3.04 (m, 0.4H), 2.91 (m, 0.6H), 2.74 (m, 0.4H), 2.20-2.43 (m, 4H), 2.02 (m, 0.6H), 1.69 (m, 6H), 1.48 (m, 4H), 1.20 (m, 1H). HPLC (Condition A): Rt 2.69 min (purity 99.9%). MS (ESI+): 456.4, MS (ESI−): 454.5.