1-Ethylhydrazinecarboxamide → 1-ethyl-1-[(E)-1-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyrazin-5-yl]ethylideneamino]urea
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.[CH2:24]([N:26]([C:28]([NH2:30])=[O:29])[NH2:27])[CH3:25]>>[CH2:24]([N:26]([C:28]([NH2:30])=[O:29])/[N:27]=[C:21](/[C:18]1[N:17]=[C:16]2[N:12]([CH2:11][C:7]3[CH:6]=[C:5]4[C:10](=[CH:9][CH:8]=3)[N:1]=[CH:2][CH:3]=[CH:4]4)[N:13]=[N:14][C:15]2=[N:20][CH:19]=1)\[CH3:22])[CH3:25]Participants
3
Procedure
The title compound was prepared in 57% yield as a white 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-ethylhydrazine-carboxamide. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.61 (s, 1H), 8.89 (d, 1H), 8.36 (d, 1H), 8.03 (s, 1H), 8.00 (d, 1H), 7.83 (d, 1H), 7.53 (m, 1H), 6.61 (d, 2H), 6.22 (s, 2H), 3.80 (q, 2H), 2.42 (s, 3H), 1.07 (t, 3H). LCMS (method B): [MH]+=390, tR=1.98 min.
Sources & evidence
- ORD record
- ord-29b5665190df4c4a83b53568c207f034
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08497368B2
Reaction notes
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