(E)-3-(dimethylamino)-1-(1-propyl-1H-pyrrolo[2,3-b]pyridin-3-yl)prop-2-en-1-one → N-(3-Nitrophenyl)-4-(1-propyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine

HRID 1875420Notes

Reaction equation

HRID 1875420 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.[N+:21]([C:24]1[CH:25]=[C:26]([NH:30][C:31]([NH2:33])=[NH:32])[CH:27]=[CH:28][CH:29]=1)([O-:23])=[O:22]>>[N+:21]([C:24]1[CH:25]=[C:26]([NH:30][C:31]2[N:33]=[C:5]([C:7]3[C:15]4[C:10](=[N:11][CH:12]=[CH:13][CH:14]=4)[N:9]([CH2:16][CH2:17][CH3:18])[CH:8]=3)[CH:4]=[CH:3][N:32]=2)[CH:27]=[CH:28][CH:29]=1)([O-:23])=[O:22]

Participants

3

Reactant 2

HCID 67445029(E)-3-(dimethylamino)-1-(1-propyl-1H-pyrrolo[2,3-b]pyridin-3-yl)prop-2-en-1-oneHCID 178479375HCID 178479375, compound

Product 1

HCID 58482948N-(3-Nitrophenyl)-4-(1-propyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine

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-(3-nitrophenyl)guanidine hydrochloride. 1H-NMR (DMSO-d6) δ: 0.90 (t, 3H, J=7.2 Hz, CH3), 1.93 (t, 2H, J=7.6 Hz, CH2), 4.33 (t, 2H, J=6.8 Hz, CH2), 7.26 (q, 1H, J=4.4 Hz, Ar—H), 7.40 (d, 1H, J=5.6 Hz, Pyrimidin-H), 7.61 (t, 1H, J=8.4 Hz, Ph-H), 7.81 (m, 1H, Ph-H), 8.12 (m, 1H, Ph-H), 8.37 (m, 1H, Ar—H), 8.48 (d, 1H, J=5.6 Hz, Pyrimidin-H), 8.64 (s, 1H, Ar—H), 8.92 (d, 1H, J=8.0 Hz, Ar—H), 9.00 (s, 1H, NH). MS (ESI+) m/z 375.1519 (M+H)+.

Sources & evidence

ORD record
ord-41320a37d3f44da19278b24345757080
Source dataset
uspto-grants-2012_11
Patent number
US08309550B2

Reaction notes

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