Dimethyl Sulfoxide → HCID 58977996, compound

Reaction equation

[CH3:1][NH:2][CH2:3][CH2:4][NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.FC1[C:18]([C:23]#[N:24])=[N:19][CH:20]=[CH:21][CH:22]=1.[CH3:25]S(C)=O>C(Cl)(Cl)Cl>[C:23]([C:18]1[C:1]([NH:2][CH2:3][CH2:4][N:5]([CH3:25])[C:6](=[O:15])[O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:22][CH:21]=[CH:20][N:19]=1)#[N:24]

Participants

Procedure

A solution of benzyl 2-(methylamino)ethylcarbamate (prepared as described in example 7, 14 g, 72.1 mmol) in DMSO (20 mL) was reacted with 3-fluoro-2-cyanopyridine (see example 2, 8 g, 65.5 mmol) in a pressure vessel at 85° C. overnight. The resulting mixture was diluted with CHCl3 (100 mL) and added to the top of a silica gel column (150 mm by 7 inches) packed with 20% EtOAc/Hexanes. The column was eluted with a gradient of 20% EtOAc/Hexanes to 100% EtOAc and the clean fractions combined and evaporated to give the product as a yellow oil.