4-((4-Methylpiperazin-1-yl)methyl)aniline → HCID 66576869, compound

HRID 1396196Notes

Reaction equation

HRID 1396196 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]([CH:16]2[CH2:18][CH2:17]2)=[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>[Cl:15][C:10]1[CH:9]=[C:8]([C:6]2[C:5]([CH:16]3[CH2:18][CH2:17]3)=[CH:4][N:3]=[C:2]([NH:31][C:30]3[CH:29]=[CH:28][C:27]([CH2:26][N:23]4[CH2:22][CH2:21][N:20]([CH3:19])[CH2:25][CH2:24]4)=[CH:33][CH:32]=3)[N:7]=2)[CH:13]=[CH:12][C:11]=1[F:14]

Participants

4

Reactant 2

HCID 31539964-((4-Methylpiperazin-1-yl)methyl)anilineHCID 86673364HCID 86673364, compound

Product 1

HCID 66576869HCID 66576869, compoundYield 51%

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-4-fluorophenyl)-5-cyclopropylpyrimidine and 4-((4-methylpiperazin-1-yl)methyl)aniline in 51% yield (yellow solid) after flash chromatography (CH2Cl2/CH3OH 99:1 gradually increasing to 95:5). 1H NMR (400 MHz, CDCl3): δ 8.22 (s, 1H), 7.90 (dd, 1H, J=7.0, 2.0 Hz), 7.72 (m, 1H), 7.55 (d, 2H, J=8.6 Hz), 7.22 (d, 1H, J=8.6 Hz), 7.09 (d, 2H, J=8.6 Hz), 3.45 (s, 2H), 2.43 (bs, 8H), 2.26 (s, 3H), 1.86 (m, 1H), 0.92 (m, 2H), 0.63 (m, 2H); MS (ESI): 452.3 [M+H]+, 226.9 [M+2H]2+.

Workup

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

Sources & evidence

ORD record
ord-f0c1e8be7676448c90a4e06b1c0a5682
Source dataset
uspto-grants-2014_12
Patent number
US08901120B2

Reaction notes

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