4-(4-Methylpiperazin-1-yl)aniline → 6-bromo-8-(2-cyclopropyl-6-fluorobenzyl)-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 1190933Notes

Reaction equation

HRID 1190933 reaction equation
[Br:1][C:2]1[C:14](=[O:15])[N:13]([CH2:16][C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[CH:24]2[CH2:26][CH2:25]2)[C:5]2[N:6]=[C:7](S(C)=O)[N:8]=[CH:9][C:4]=2[CH:3]=1.[CH3:27][N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=2)[CH2:30][CH2:29]1>>[Br:1][C:2]1[C:14](=[O:15])[N:13]([CH2:16][C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[CH:24]2[CH2:26][CH2:25]2)[C:5]2[N:6]=[C:7]([NH:38][C:37]3[CH:36]=[CH:35][C:34]([N:31]4[CH2:30][CH2:29][N:28]([CH3:27])[CH2:33][CH2:32]4)=[CH:40][CH:39]=3)[N:8]=[CH:9][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 679972076-bromo-8-(2-cyclopropyl-6-fluorobenzyl)-2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 679971896-bromo-8-(2-cyclopropyl-6-fluorobenzyl)-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-8H-pyrido[2,3-d]pyrimidin-7-oneYield 55%

Procedure

6-Bromo-8-(2-cyclopropyl-6-fluorobenzyl)-2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one (9, 385 mg, 0.9 mmol) and 4-(4-methylpiperazino)aniline (169 mg, 0.9 mmol) were stirred at 140° C. for 6 h. The reaction mixture was purified by column chromatography using dichloromethane:methanol (100:1→100:3→100:5) to yield the title compound as a yellow solid (272 mg, 0.48 mmol, 55%). ESMS m/z 563 (M+H)+.

Workup

  1. customThe reaction mixture was purified by column chromatography

Sources & evidence

ORD record
ord-98bcb71f2235452c852c33e226952dd6
Source dataset
uspto-grants-2014_03
Patent number
US08680099B2

Reaction notes

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