4-((4-Methylpiperazin-1-yl)methyl)aniline → HCID 70683482, compound

HRID 1396204Notes

Reaction equation

HRID 1396204 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])[C:5]([Cl:22])=[CH:4][N:3]=1.[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([CH2:30][C:31]2[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=2)[CH2:26][CH2:25]1>C(Cl)Cl.CO>[Cl:22][C:5]1[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])=[N:7][C:2]([NH:35][C:34]2[CH:33]=[CH:32][C:31]([CH2:30][N:27]3[CH2:26][CH2:25][N:24]([CH3:23])[CH2:29][CH2:28]3)=[CH:37][CH:36]=2)=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 31539964-((4-Methylpiperazin-1-yl)methyl)anilineHCID 86673367HCID 86673367, compound

Product 1

HCID 70683482HCID 70683482, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared according to synthesis procedure B described above from (2-((2,5-dichloropyrimidin-4-yl)amino)phenyl)(pyrrolidin-1-yl)methanone and 4-((4-methylpiperazin-1-yl)methyl)aniline in 73% yield (yellow solid) after flash chromatography (CH2Cl2/CH3OH 99:1 gradually increasing to 95:5). 1H NMR (400 MHz, CDCl3): δ 9.68 (s, 1H), 8.40 (d, 1H, J=8.2 Hz), 8.04 (s, 1H), 7.46 (d, 2H, J=8.2 Hz), 7.39-7.34 (m, 2H), 7.21 (d, 2H, J=8.2 Hz), 7.06 (t, 1H, J=7.5 Hz), 3.65 (t, 2H, J=7.0 Hz), 3.48 (t, 2H, J=6.3 Hz), 3.44 (s, 2H), 2.44 (bs, 8H), 2.26 (s, 3H), 1.95 (m, 2H), 1.83 (m, 2H); MS (ESI): 506.1 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-6b5dffe7dbc64016980dee2aeed4f9b0
Source dataset
uspto-grants-2014_12
Patent number
US08901120B2

Reaction notes

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