3-(4-Methylpiperazin-1-yl)aniline → 7-[3-(1,1-Dioxido-1,2-thiazolidin-2-yl)phenyl]-N-[3-(4-methylpiperazin-1-yl)phenyl]pyrrolo[2,1-f][1,2,4]triazin-2-amine

HRID 1262412Notes

Reaction equation

HRID 1262412 reaction equation
[O:1]=[S:2]1(=[O:25])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:8]=[C:9]([C:13]2[N:21]3[C:16]([CH:17]=[N:18][C:19](S(C)=O)=[N:20]3)=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1.[CH3:26][N:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:34]=[C:35]([CH:37]=[CH:38][CH:39]=2)[NH2:36])[CH2:29][CH2:28]1>>[O:1]=[S:2]1(=[O:25])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:8]=[C:9]([C:13]2[N:21]3[C:16]([CH:17]=[N:18][C:19]([NH:36][C:35]4[CH:37]=[CH:38][CH:39]=[C:33]([N:30]5[CH2:29][CH2:28][N:27]([CH3:26])[CH2:32][CH2:31]5)[CH:34]=4)=[N:20]3)=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 115646133-(4-Methylpiperazin-1-yl)anilineHCID 667121237-[3-(1,1-Dioxido-1,2-thiazolidin-2-yl)phenyl]-2-(methylsulfinyl)pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 468529667-[3-(1,1-Dioxido-1,2-thiazolidin-2-yl)phenyl]-N-[3-(4-methylpiperazin-1-yl)phenyl]pyrrolo[2,1-f][1,2,4]triazin-2-amineYield 20.8%

Procedure

Analogous to Example 1491c, 7-[3-(1,1-Dioxido-1,2-thiazolidin-2-yl)phenyl]-2-(methylsulfinyl)pyrrolo[2,1-f][1,2,4]triazine (90.0 mg, 0.239 mmol) and 3-(4-Methylpiperazin-1-yl)aniline (91.4 mg, 0.478 mmol) were reacted to afford 7-[3-(1,1-Dioxido-1,2-thiazolidin-2-yl)phenyl]-N-[3-(4-methylpiperazin-1-yl)phenyl]pyrrolo[2,1-f][1,2,4]triazin-2-amine (25 mg, 18%). LCMS (HPLC): 0.84 min, m/z=504 (M+H); 1H-NMR (DMSO-d6): 9.29 (s, 1H), 8.99 (s, 1H), 7.86 (d, 1H, J=7.8 Hz), 7.75 (s, 1H), 7.49 (m, 1H), 7.32 (m, 2H), 7.18 (d, 1H, J=8.0 Hz), 7.11 (m, 2H), 6.96 (d, 1H, J=4.7 Hz), 6.56 (d, 1H, J=7.8 Hz), 3.73 (t, 2H, J=6.4 Hz), 3.52 (t, 2H, J=7.4 Hz), 2.99 (m, 4H), 2.37 (m, 6H), 2.20 (s, 3H).

Sources & evidence

ORD record
ord-d2b277ffc04d4a249fbdb8900904bced
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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