4-((4-Methylpiperazin-1-yl)methyl)aniline → HCID 66576871, compound

HRID 1396197Notes

Reaction equation

HRID 1396197 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([Cl:18])[CH:9]=2)[C:5]([CH3:19])=[CH:4][N:3]=1.[CH3:20][N:21]1[CH2:26][CH2:25][N:24]([CH2:27][C:28]2[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=2)[CH2:23][CH2:22]1>C(Cl)Cl.CO>[Cl:18][C:10]1[CH:9]=[C:8]([C:6]2[C:5]([CH3:19])=[CH:4][N:3]=[C:2]([NH:32][C:31]3[CH:30]=[CH:29][C:28]([CH2:27][N:24]4[CH2:23][CH2:22][N:21]([CH3:20])[CH2:26][CH2:25]4)=[CH:34][CH:33]=3)[N:7]=2)[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=1

Participants

4

Reactant 2

HCID 31539964-((4-Methylpiperazin-1-yl)methyl)anilineHCID 86673365HCID 86673365, compound

Product 1

HCID 66576871HCID 66576871, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared according to synthesis procedure B described above from 2-chloro-4-(3-chloro-5-(trifluoromethyl)phenyl)-5-methylpyrimidine and 4-((4-methylpiperazin-1-yl)methyl)aniline in 76% 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), 7.79 (d, 2H, J=7.8 Hz), 7.69 (s, 1H), 7.55 (d, 2H, J=8.2 Hz), 7.26 (d, 2H, J=8.6 Hz), 3.47 (s, 2H), 2.50 (bs, 8H), 2.31 (s, 3H), 2.25 (s, 3H); MS (ESI): 476.3 [M+H]+, 238.7 [M+2H]2+.

Workup

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

Sources & evidence

ORD record
ord-e9c67d2a221844bf8ea0195be8193a6b
Source dataset
uspto-grants-2014_12
Patent number
US08901120B2

Reaction notes

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