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

HRID 1261900Notes

Reaction equation

HRID 1261900 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.[CH2:24]1[N:29]([C:30]2[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=2)[CH2:28][CH2:27][O:26][CH2:25]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:36][C:33]1[CH:32]=[CH:31][C:30]([N:29]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)=[CH:35][CH:34]=1)=[N:6]2

Participants

4

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 667113545-Bromo-2-methanesulfinyl-7-(4-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1, 2,4]triazine

Product 1

HCID 66710757[5-Bromo-7-(4-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(4-morpholin-4-yl-phenyl)-amineYield 67%

Conditions

Temperature
150 °C

Procedure

Into a 30 mL vial, [A] 5-Bromo-2-methanesulfinyl-7-(4-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (0.14 g, 0.00034 mol), 4-(4-morpholino)aniline (0.181 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-morpholin-4-yl-phenyl)-amine as a yellow solid (120 mg, 67%). MP 242-244° C. LCMS (E/I+) 451.23 (M+H). NMR 1H (DSMO-d6)-9.43 (s, 1H), 8.86 (s, 1H), 8.16 (d, 2H, J=7.76 Hz), 7.62 (d, 2H, J=8.93 Hz), 7.54 (t, 1H, J=7.77 Hz), 7.41 (t, 1H, J=7.16 Hz), 7.34 (s, 1H), 6.93 (d, 2H, J=8.97 Hz), 3.74 (t, 4H, J=4.29 Hz), 3.06 (t, 4H, J=4.64 Hz).

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-20f28836e3ba4ba9a51056ad3ecbed76
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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