4-((4-Methylpiperazin-1-yl)methyl)aniline → HCID 66576708, compound

HRID 1396186Notes

Reaction equation

HRID 1396186 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([Cl:15])[CH:9]=2)[C:5]([CH3:16])=[CH:4][N:3]=1.[CH3:17][N:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=2)[CH2:20][CH2:19]1>>[Cl:15][C:10]1[CH:9]=[C:8]([C:6]2[C:5]([CH3:16])=[CH:4][N:3]=[C:2]([NH:29][C:28]3[CH:27]=[CH:26][C:25]([CH2:24][N:21]4[CH2:20][CH2:19][N:18]([CH3:17])[CH2:23][CH2:22]4)=[CH:31][CH:30]=3)[N:7]=2)[CH:13]=[CH:12][C:11]=1[F:14]

Participants

3

Reactant 2

HCID 31539964-((4-Methylpiperazin-1-yl)methyl)anilineHCID 86673359HCID 86673359, compound

Product 1

HCID 66576708HCID 66576708, compoundYield 84%

Procedure

The title compound was prepared according to synthesis procedure B described above from 2-chloro-4-(3-chloro-4-fluorophenyl)-5-methylpyrimidine and 4-((4-methylpiperazin-1-yl)methyl)aniline in 84% yield (yellow solid) after purification by flash chromatography (CH2Cl2/CH3OH 99:1 gradually increasing to 95:5). 1H NMR (400 MHz, CDCl3): δ 8.30 (s, 1H), 7.70 (m, 1H), 7.56 (d, 2H, J=8.6 Hz), 7.51 (m, 1H), 7.25 (d, 2H, J: not calculated due to overlapping peaks), 7.05 (s, 1H), 3.46 (s, 2H), 2.46 (bs, 8H), 2.28 (s, 3H), 2.25 (s, 3H); MS (ESI): 426.3 [M+H]+, 213.7 [M+2H]2+.

Workup

  1. customaccording to synthesis procedure B
  2. customafter purification by flash chromatography (CH2Cl2/CH3OH 99:1
  3. temperaturegradually increasing to 95:5)

Sources & evidence

ORD record
ord-a06eaa661ec14293a49d1140e7fb1380
Source dataset
uspto-grants-2014_12
Patent number
US08901120B2

Reaction notes

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