N-methyl-2-pyrrolidone → [5-Bromo-7-(4-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine

HRID 1261892Notes

Reaction equation

HRID 1261892 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[N:5]2[C:10]=1[CH:9]=[N:8][C:7](S(C)=O)=[N:6]2.[CH3:24][N:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=2)[CH2:27][CH2:26]1.CN1CCCC1=O>>[Br:1][C:2]1[CH:3]=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[N:5]2[C:10]=1[CH:9]=[N:8][C:7]([NH:37][C:34]1[CH:33]=[CH:32][C:31]([N:28]3[CH2:27][CH2:26][N:25]([CH3:24])[CH2:30][CH2:29]3)=[CH:36][CH:35]=1)=[N:6]2

Participants

4

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 667113545-Bromo-2-methanesulfinyl-7-(4-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1, 2,4]triazine

Product 1

HCID 66710869[5-Bromo-7-(4-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amineYield 44%

Conditions

Temperature
150 °C

Procedure

Into a 30 mL vial, 5-Bromo-2-methanesulfinyl-7-(4-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (0.14 g, 0.00034 mol), 4-(4-Methyl-piperazin-1-yl)-phenylamine (0.194 g, 0.00101 mol), and N-Methylpyrrolidinone (0.22 mL, 0.0023 mol) were added. The mixture was heated at 150° C. for 3 hours. The mixture was purified via ISCO column chromatography with DCM and MeOH as eluant (0 to 15% methanol). The collected fractions afforded [5-Bromo-7-(4-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine as a yellow solid (80 mg, 44%). MP 265-266° C. LCMS (E/I+) 543.11 (M+H). NMR 1H (DSMO-d6)-9.49 (s, 1H), 8.93 (s, 1H), 8.45 (d, 2H, J=8.56 Hz), 8.03 (d, 2H, J=8.60 Hz), 7.55 (d, 2H, J=9.01 Hz), 7.35 (s, 1H), 6.96 (d, 2H, J=9.08 Hz), 3.39 (s, 3H), 3.10 (t, 4H, J=5.00 Hz), 2.47 (t, 4H, J=5.13 Hz), 2.23 (s, 3H).

Workup

  1. customThe mixture was purified via ISCO column chromatography with DCM and MeOH as eluant (0 to 15% methanol)

Sources & evidence

ORD record
ord-3908dde521324f8391210d419e907e55
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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