(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)benzonitrile
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.[C:20]([C:22]1[CH:23]=[C:24]([NH:28][C:29]([NH2:31])=[NH:30])[CH:25]=[CH:26][CH:27]=1)#[N: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:31]=[C:29]([NH:28][C:24]3[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=3)[C:20]#[N:21])[N:30]=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-cyanophenyl)guanidine hydrochloride. 1H-NMR (DMSO-d6) δ: 1.48 (t, 3H, J=7.2 Hz, CH3), 4.39 (q, 2H, J=7.2 Hz, CH2), 7.27 (m, 1H, Ar—H), 7.36 (d, 1H, J=4.4 Hz, Pyrimidin-H), 7.42 (m, 1H, Ph-H or Ar—H), 7.51 (m, 1H, Ph-H or Ar—H), 7.98 (m, 1H, Ar—H), 8.38 (m, 1H, Ph-H or Ar—H), 8.46 (m, 2H, Pyrimidin-H or Ar—H), 8.63 (s, 1H, Ar—H), 8.94 (m, 1H, Ph-H or Ar—H), 9.85 (s, 1H, NH). MS (ESI+) m/z 341.1489 (M+H)+.
Sources & evidence
- ORD record
- ord-13a06c9f8059492fb4e9102a1afdb0b6
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08309550B2
Reaction notes
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