4-(Pyridin-3-yl)aniline → (4-Pyridin-3-yl-phenyl)-{7-[3-(pyrrolidine-1-sulfonyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-yl}-amine

HRID 1262251Notes

Reaction equation

HRID 1262251 reaction equation
[N:1]1([S:6]([C:9]2[CH:10]=[C:11]([C:15]3[N:23]4[C:18]([CH:19]=[N:20][C:21](O)=[N:22]4)=[CH:17][CH:16]=3)[CH:12]=[CH:13][CH:14]=2)(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]2[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=2)[CH:26]=1>>[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]2[CH:36]=[CH:35][C:34]([NH:37][C:21]3[N:20]=[CH:19][C:18]4=[CH:17][CH:16]=[C:15]([C:11]5[CH:12]=[CH:13][CH:14]=[C:9]([S:6]([N:1]6[CH2:5][CH2:4][CH2:3][CH2:2]6)(=[O:8])=[O:7])[CH:10]=5)[N:23]4[N:22]=3)=[CH:33][CH:32]=2)[CH:26]=1

Participants

3

Reactant 2

HCID 4595224-(Pyridin-3-yl)anilineHCID 1785273247-[3-(Pyrrolidine-1-sulfonyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-ol

Product 1

HCID 46851708(4-Pyridin-3-yl-phenyl)-{7-[3-(pyrrolidine-1-sulfonyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-yl}-amine

Procedure

(4-Pyridin-3-yl-phenyl)-{7-[3-(pyrrolidine-1-sulfonyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-yl}-amine was prepared from 7-[3-(pyrrolidine-1-sulfonyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-ol and 4-pyridin-3-yl-phenylamine in an analogous manner to Example 1052a. Product isolated as a yellow solid (88 mg, 58%). m.p.=194-200° C.; LCMS (m/e) 497 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.87 (s, 1H), 8.78 (s, 1H), 8.56 (d, 1H, J=4.3 Hz), 8.53 (s, 1H), 8.43 (d, 1H, J=8.0 Hz), 7.91 (d, 1H, J=8.0 Hz), 7.84 (d, 1H, J=7.8 Hz), 7.74 (d, 1H, J=8.6 Hz), 7.71-7.61 (m, 3H), 7.35 (dd, 1H, J=4.9 and 7.7 Hz), 7.09 (d, 1H, J=4.8 Hz), 6.98 (s, 1H), 6.89 (d, 1H, J=4.8 Hz), 3.36-3.22 (m, 4H), 1.83-1.72 (m, 4H).

Sources & evidence

ORD record
ord-b27ef885edad49efabe2c55c2b62fa09
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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