4-((4-Methylpiperazin-1-yl)methyl)aniline → HCID 66576787, compound

HRID 1396191Notes

Reaction equation

HRID 1396191 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:9]=2)[C:5]([CH3:18])=[CH:4][N:3]=1.[CH3:19][N:20]1[CH2:25][CH2:24][N:23]([CH2:26][C:27]2[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=2)[CH2:22][CH2:21]1>C(Cl)Cl.CO>[CH3:18][C:5]1[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:9]=2)=[N:7][C:2]([NH:31][C:30]2[CH:29]=[CH:28][C:27]([CH2:26][N:23]3[CH2:22][CH2:21][N:20]([CH3:19])[CH2:25][CH2:24]3)=[CH:33][CH:32]=2)=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 31539964-((4-Methylpiperazin-1-yl)methyl)anilineHCID 86673361HCID 86673361, compound

Product 1

HCID 66576787HCID 66576787, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared according to synthesis procedure B described above from 2-chloro-5-methyl-4-(3-(methylsulfonyl)phenyl)pyrimidine and 4-((4-methylpiperazin-1-yl)methyl)aniline in 63% yield (yellow solid) after flash chromatography (CH2Cl2/CH3OH 99:1 gradually increasing to 95:5). 1H NMR (400 MHz, CDCl3): δ 8.35 (s, 1H), 8.23 (s, 1H), 8.03 (d, 1H, J=7.8 Hz), 7.93 (d, 1H, J=7.8 Hz), 7.70 (t, 1H, J=7.8 Hz), 7.56 (d, 2H, J=8.2 Hz), 7.26 (d, 2H, J: not calculated due to overlapping peaks), 3.45 (s, 2H), 3.09 (s, 3H), 2.43 (bs, 8H), 2.26 (s, 6H). MS (ESI): 452.3 [M+H]+, 226.8 [M+2H]2+.

Workup

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

Sources & evidence

ORD record
ord-78baaeb484994fce9a51efc845ee4fd1
Source dataset
uspto-grants-2014_12
Patent number
US08901120B2

Reaction notes

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