(E)-3-(dimethylamino)-1-(1-ethyl-1H-pyrrolo[2,3-b]pyridin-3-yl)prop-2-en-1-one → 3-(4-(1-Ethyl-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][CH3:17])[CH:8]=1)=O.Cl.[OH:20][C:21]1[CH:22]=[C:23]([NH:27][C:28]([NH2:30])=[NH:29])[CH:24]=[CH:25][CH:26]=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:30]=[C:28]([NH:27][C:23]3[CH:22]=[C:21]([OH:20])[CH:26]=[CH:25][CH:24]=3)[N:29]=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-hydroxyphenyl)guanidine hydrochloride. 1H-NMR (DMSO-d6) δ: 1.18 (t, 3H, J=7.2 Hz, CH3), 4.37 (q, 2H, J=7.2 Hz, CH2), 6.40 (m, 1H, Ph-H), 7.08 (t, 1H, J=7.6 Hz, Ph-H), 7.18 (m, 1H, Ar—H), 7.24 (d, 1H, J=5.6 Hz, Pyrimidin-H), 7.37 (s, 1H, Ph-H), 8.36 (m, 2H, Pyrimidin-H and Ar—H), 8.59 (s, 1H, Ar—H), 9.00 (d, 1H, J=8.0 Hz, Ph-H), 9.24 (s, 1H, Ar—H), 9.33 (s, 1H, NH). MS (ESI+) m/z 332.1355 (M+H)+.
Sources & evidence
- ORD record
- ord-b2728e612ce948409bf100826ae15e04
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08309550B2
Reaction notes
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