1-Aminoimidazolidin-2-one → 1-[(E)-1-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyrazin-5-yl]ethylideneamino]imidazolidin-2-one
Reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[C:16]4=[N:17][C:18]([C:21](=O)[CH3:22])=[CH:19][N:20]=[C:15]4[N:14]=[N:13]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH2:24][N:25]1[CH2:29][CH2:28][NH:27][C:26]1=[O:30]>>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[C:16]4=[N:17][C:18](/[C:21](=[N:24]/[N:25]5[CH2:29][CH2:28][NH:27][C:26]5=[O:30])/[CH3:22])=[CH:19][N:20]=[C:15]4[N:14]=[N:13]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1Participants
3
Procedure
The title compound was prepared in 26% yield as a light yellow solid in analogy to the synthesis of example 52 from 1-(1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone and 1-aminoimidazolidin-2-one. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.42 (s, 1H), 8.89 (d, 1H), 8.35 (d, 1H), 8.02 (m, 2H), 7.84 (d, 1H), 7.53 (dd, 1H), 7.36 (s, 1H), 6.22 (s, 2H), 3.75 (t, 2H), 3.41 (t, 2H), 2.42 (s, 3H). LCMS (method B): [MH]+=388, tR=1.89 min.