(E)-3-(dimethylamino)-1-(1-ethyl-1H-pyrrolo[2,3-b]pyridin-3-yl)prop-2-en-1-one → 4-(1-Ethyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(3-nitrophenyl)pyrimidin-2-amine
Reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:16][CH3:17])[CH:8]=1)=O.Cl.[N+:20]([C:23]1[CH:24]=[C:25]([NH:29][C:30]([NH2:32])=[NH:31])[CH:26]=[CH:27][CH:28]=1)([O-:22])=[O:21]>>[CH2:16]([N:9]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:15]2[C:7]([C:5]2[CH:4]=[CH:3][N:32]=[C:30]([NH:29][C:25]3[CH:26]=[CH:27][CH:28]=[C:23]([N+:20]([O-:22])=[O:21])[CH:24]=3)[N:31]=2)=[CH:8]1)[CH3:17]Participants
3
Procedure
Prepared by treatment of (E)-3-(dimethylamino)-1-(1-ethyl-1H-pyrrolo[2,3-b]pyridin-3-yl)prop-2-en-1-one and 1-(3-nitrophenyl)guanidine hydrochloride. 1H-NMR (DMSO-d6) δ: 1.49 (t, 3H, J=7.2 Hz, CH3), 4.37 (q, 2H, J=7.6 Hz, CH2), 7.26 (m, 1H, Ar—H), 7.39 (d, 1H, J=5.2 Hz, Pyrimidin-H), 7.61 (t, 1H, J=8.0 Hz, Ph-H), 7.83 (m, 1H, Ar—H), 8.12 (d, 1H, J=8.0 Hz, Ph-H), 8.38 (m, 1H, Ar—H), 8.49 (d, 1H, J=5.2 Hz, Pyrimidin-H), 8.62 (s, 1H, Ph-H), 8.92 (d, 1H, J=8.0 Hz, Ph-H), 9.01 (s, 1H, Ar—H). MS (ESI+) m/z 361.1308 (M+H)+.
Sources & evidence
- ORD record
- ord-890769646b61492c9e10c010d022bf94
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08309550B2
Reaction notes
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