4-((4-Methylpiperazin-1-yl)methyl)aniline → HCID 66576868, compound

HRID 1396195Notes

Reaction equation

HRID 1396195 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]([F:18])([F:17])[F:16])[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>[CH3:19][C:5]1[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]([F:18])([F:17])[F:16])[CH:9]=2)=[N:7][C:2]([NH:32][C:31]2[CH:30]=[CH:29][C:28]([CH2:27][N:24]3[CH2:23][CH2:22][N:21]([CH3:20])[CH2:26][CH2:25]3)=[CH:34][CH:33]=2)=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 31539964-((4-Methylpiperazin-1-yl)methyl)anilineHCID 79078919HCID 79078919, compound

Product 1

HCID 66576868HCID 66576868, compoundYield 79%

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-(trifluoromethoxy)phenyl)pyrimidine and 4-((4-methylpiperazin-1-yl)methyl)aniline in 79% yield (yellow solid) after flash chromatography (CH2Cl2/CH3OH 99:1 gradually increasing to 95:5). 1H NMR (400 MHz, CDCl3): δ 8.32 (s, 1H), 7.57 (d, 3H, J=8.5 Hz), 7.52 (s, 1H), 7.50 (t, 1H, J=7.9 Hz), 7.29 (d, 1H, J=7.9 Hz), 7.25 (d, 2H, J: not calculated due to overlapping peaks), 3.45 (s, 2H), 2.47 (bs, 8H), 2.28 (s, 3H), 2.26 (s, 3H); MS (ESI): 458.3 [M+H]+, 229.7 [M+2H]2+.

Workup

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

Sources & evidence

ORD record
ord-b98a1c3ae5704251ac8dc4f4b7418fb7
Source dataset
uspto-grants-2014_12
Patent number
US08901120B2

Reaction notes

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