(E)-3-(dimethylamino)-1-(1-propyl-1H-pyrrolo[2,3-b]pyridin-3-yl)prop-2-en-1-one → 4-(4-(1-Propyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-ylamino)phenol
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][CH2:17][CH3:18])[CH:8]=1)=O.Cl.[OH:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([NH2:31])=[NH:30])=[CH:24][CH:23]=1>>[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:31]=[C:29]([NH:28][C:25]3[CH:26]=[CH:27][C:22]([OH:21])=[CH:23][CH:24]=3)[N:30]=2)=[CH:8]1)[CH2:17][CH3:18]Participants
3
Procedure
Prepared by treatment of (E)-3-(dimethylamino)-1-(1-propyl-1H-pyrrolo[2,3-b]pyridin-3-yl)prop-2-en-1-one with 1-(4-hydroxyphenyl)guanidine hydrochloride. 1H-NMR (DMSO-d6) δ: 0.88 (t, 3H, J=7.2 Hz, CH3), 1.90 (t, 2H, J=7.6 Hz, CH2), 4.30 (t, 2H, J=6.8 Hz, CH2), 6.74 (m, 2H, Ph-H), 7.16 (d, 1H, J=5.6 Hz, Pyrimidin-H), 7.20 (t, 1H, J=4.8 Hz, Ar—H), 7.51 (m, 2H, Ph-H), 8.30 (d, 1H, J=5.6 Hz, Pyrimidin-H), 8.35 (m, 1H, Ar—H), 8.52 (s, 1H, Ar—H), 8.88 (d, 1H, J=7.6 Hz, Ar—H), 9.05 (s, 1H, NH), 9.11 (s, 1H, OH). MS (ESI+) m/z 346.1659 (M+H)+.
Sources & evidence
- ORD record
- ord-d650168d1df24c9fa4a615907683cdfe
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08309550B2
Reaction notes
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