4-((4-Methylpiperazin-1-yl)methyl)aniline → 2-((5-chloro-2-((4-((4-methylpiperazin-1-yl)methyl)phenyl)amino)pyrimidin-4-yl)amino)-N,N-dimethylbenzamide

HRID 1396203Notes

Reaction equation

HRID 1396203 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=2[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[C:5]([Cl:20])=[CH:4][N:3]=1.[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([CH2:28][C:29]2[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=2)[CH2:24][CH2:23]1>C(Cl)Cl.CO>[Cl:20][C:5]1[C:6]([NH:8][C:9]2[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=2[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])=[N:7][C:2]([NH:33][C:32]2[CH:31]=[CH:30][C:29]([CH2:28][N:25]3[CH2:24][CH2:23][N:22]([CH3:21])[CH2:27][CH2:26]3)=[CH:35][CH:34]=2)=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 31539964-((4-Methylpiperazin-1-yl)methyl)anilineHCID 579741612-[(2,5-dichloropyrimidin-4-yl)amino]-N,N-dimethylbenzamide

Product 1

HCID 683850492-((5-chloro-2-((4-((4-methylpiperazin-1-yl)methyl)phenyl)amino)pyrimidin-4-yl)amino)-N,N-dimethylbenzamideYield 32%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared according to synthesis procedure B described above from 2-((2,5-dichloropyrimidin-4-yl)amino)-N,N-dimethylbenzamide and 4-((4-methylpiperazin-1-yl)methyl)aniline in 32% yield (yellow solid) after flash chromatography (CH2Cl2/CH3OH 99:1 gradually increasing to 95:5). 1H NMR (400 MHz, CDCl3): δ 9.07 (s, 1H), 8.35 (d, 1H J=8.2 Hz), 8.05 (s, 1H), 7.46 (s, 2H, J=8.2 Hz), 7.38 (t, 1H, J=7.8 Hz), 7.29 (d, 1H, J=7.5 Hz), 7.21 (d, 2H, J=8.2 Hz), 7.10 (t, 1H, J=7.5 Hz), 7.01 (s, 1H), 3.45 (s, 2H), 3.11 (s, 3H), 3.04 (s, 3H), 2.43 (bs, 8H), 2.27 (s, 3H); MS (ESI): 480.1 [M+H]+.

Workup

  1. customaccording to synthesis procedure B
  2. temperaturegradually increasing to 95:5)

Sources & evidence

ORD record
ord-c26638aa0f834f94b95b1564d4e793c6
Source dataset
uspto-grants-2014_12
Patent number
US08901120B2

Reaction notes

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