4-((4-Methylpiperazin-1-yl)methyl)aniline → HCID 66576785, compound

HRID 1396187Notes

Reaction equation

HRID 1396187 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[C:5]([CH3:15])=[CH:4][N:3]=1.[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=2)[CH2:19][CH2:18]1>>[F:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[C:5]([CH3:15])=[CH:4][N:3]=[C:2]([NH:28][C:27]3[CH:26]=[CH:25][C:24]([CH2:23][N:20]4[CH2:19][CH2:18][N:17]([CH3:16])[CH2:22][CH2:21]4)=[CH:30][CH:29]=3)[N:7]=2)=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 31539964-((4-Methylpiperazin-1-yl)methyl)anilineHCID 79072654HCID 79072654, compound

Product 1

HCID 66576785HCID 66576785, compoundYield 79%

Procedure

The title compound was prepared according to procedure B from 2-chloro-4-(4-fluorophenyl)-5-methylpyrimidine and 4-((4-methylpiperazin-1-yl)methyl)aniline in 79% yield (yellow solid) after purification by flash chromatography (CH2Cl2/CH3OH 99:1 gradually increasing to 95:5). 1H NMR (400 MHz, CDCl3): δ 8.28 (s, 1H), 7.63 (m, 2H), 7.55 (d, 2H, J=8.5 Hz), 7.22 (t, 2H, J=8.7 Hz), 7.14 (t, 2H, J=8.7 Hz), 3.44 (s, 2H), 2.42 (bs, 8H), 2.25 (s, 3H), 2.24 (s, 3H); MS (ESI): 392.0 [M+H]+, 196 [M+H]2+.

Workup

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

Sources & evidence

ORD record
ord-18079e10fa384ad3a7c44f4a6b73c9ff
Source dataset
uspto-grants-2014_12
Patent number
US08901120B2

Reaction notes

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