Nitrogen → HCID 86690313, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:34])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:15]2=[N:16][C:17]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)[N:19]=[C:14]2[CH:13]=[CH:12]1)[CH3:2].N#N.O=P(Cl)(Cl)Cl.CN([CH:45]=[O:46])C>>[CH:45]([C:13]1[C:14]2[C:15](=[N:16][C:17]([C:27]3[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=3)=[C:18]([C:20]3[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=3)[N:19]=2)[N:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:34])[CH:12]=1)=[O:46]Participants
5
Procedure
A mixture comprising 7-(2,3-di-p-tolyl-pyrrolo[2,3-b]pyrazin-5-yl)-heptanoic acid ethyl ester (Intermediate B) (479 mg, 1.051 mmol) in anhydrous DMF (1 ml) was degassed with N2 and treated dropwise with POCl3 (0.147 ml, 1.577 mmol). The mixture was stirred at room temperature for 3 hours and treated with a further portion of POCl3 (0.147 ml, 1.577 mmol). After stirring at RT for 16 hours, the mixture was partitioned between water (100 ml) and EtOAc (20 ml) and the pH of the bi-phasic solution was adjusted to pH 8-9 using sat. NaHCO3 solution. The aqueous portion was extracted with EtOAc (×3) and the combined organic extract were washed with water (×1), brine (×1), dried over MgSO4 and filtered and concentrated under reduced pressure to afford the titled compound as a brown oil;