(E)-1-(7-chloro-1-ethyl-1H-pyrrolo[2,3-c]pyridin-3-yl)-3-(dimethylamino)prop-2-en-1-one → 3-(4-(7-Chloro-1-ethyl-1H-pyrrolo[2,3-c]pyridin-3-yl)pyrimidin-2-ylamino)phenol

HRID 1875427Notes

Reaction equation

HRID 1875427 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:10]([C:11](=O)/[CH:12]=[CH:13]/N(C)C)=[CH:9][N:8]([CH2:18][CH3:19])[C:7]=12.Cl.[OH:21][C:22]1[CH:23]=[C:24]([NH:28][C:29]([NH2:31])=[NH:30])[CH:25]=[CH:26][CH:27]=1>>[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:10]([C:11]3[CH:12]=[CH:13][N:31]=[C:29]([NH:28][C:24]4[CH:23]=[C:22]([OH:21])[CH:27]=[CH:26][CH:25]=4)[N:30]=3)=[CH:9][N:8]([CH2:18][CH3:19])[C:7]=12

Participants

3

Reactant 2

HCID 86658650(E)-1-(7-chloro-1-ethyl-1H-pyrrolo[2,3-c]pyridin-3-yl)-3-(dimethylamino)prop-2-en-1-oneHCID 178479376HCID 178479376, compound

Product 1

HCID 461950893-(4-(7-Chloro-1-ethyl-1H-pyrrolo[2,3-c]pyridin-3-yl)pyrimidin-2-ylamino)phenol

Procedure

Prepared by treatment of (E)-1-(7-chloro-1-ethyl-1H-pyrrolo[2,3-c]pyridin-3-yl)-3-(dimethylamino)prop-2-en-1-one with 1-(3-hydroxyphenyl)guanidine hydrochloride. 1H-NMR (DMSO-d6) δ: 1.46 (m, 3H, CH3), 4.49 (m, 2H, CH2), 6.39 (m, 1H, Ph-H), 7.07 (m, 1H, Ph-H), 7.20 (m, 2H, Ph-H and Ar—H), 7.77 (d, 1H, J=5.6 Hz, Pyrimidin-H), 8.18 (d, 1H, J=5.6 Hz, Ar—H), 8.37 (d, 1H, J=5.6 Hz, Pyrimidin-H), 8.41 (s, 1H, Ar—H), 9.23 (s, 1H, OH), 9.32 (s, 1H, NH). MS (ESI+) m/z 362.1670 (M+H)+

Sources & evidence

ORD record
ord-ef4ff46eec7843d0961855a72f7d792a
Source dataset
uspto-grants-2012_11
Patent number
US08309550B2

Reaction notes

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