Pyridine → HCID 11360085, compound

Reaction equation

N1C=CC=CC=1.[NH:7]1[CH2:12][CH2:11][CH:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[N:14]=2)[CH2:9][CH2:8]1.[CH2:24]([S:28](Cl)(=[O:30])=[O:29])[CH2:25][CH2:26][CH3:27]>C(Cl)Cl>[CH2:24]([S:28]([N:7]1[CH2:12][CH2:11][CH:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[N:14]=2)[CH2:9][CH2:8]1)(=[O:30])=[O:29])[CH2:25][CH2:26][CH3:27]

Participants

Procedure

A solution of pyridine (18 μl, 0.22 mmol) and 4-(5-piperidin-4-yl-[1,2,4]oxadiazol-3-yl)pyridine (Example 51, 50 mg, 0.22 mmol) in CH2Cl2 (4 ml) was treated with butane-1-sulfonyl chloride (56 μl, 0.43 mmol). The reaction was stirred at rt for 18 h then quenched with saturated aqueous NaHCO3 (1 ml). The organic phase was separated, dried (MgSO4) and evaporated. The residue was dissolved in EtOAc (5 ml) and extracted into 2M HCl (10 ml). The aqueous phase was then basified using 2M NaOH to pH=8 and extracted with CH2Cl2 (2×10 ml). The combined organic phases were dried (MgSO4) and evaporated to afford the title compound: RT=3.29 min, m/z (ES+)=351.2 [+H]+.