4-((4-Methylpiperazin-1-yl)methyl)aniline → HCID 70683483, compound

HRID 1396206Notes

Reaction equation

HRID 1396206 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[S:16]([N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)(=[O:18])=[O:17])[C:5]([Cl:24])=[CH:4][N:3]=1.[CH3:25][N:26]1[CH2:31][CH2:30][N:29]([CH2:32][C:33]2[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=2)[CH2:28][CH2:27]1>C(Cl)Cl.CO>[Cl:24][C:5]1[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[S:16]([N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)(=[O:18])=[O:17])=[N:7][C:2]([NH:37][C:36]2[CH:35]=[CH:34][C:33]([CH2:32][N:29]3[CH2:28][CH2:27][N:26]([CH3:25])[CH2:31][CH2:30]3)=[CH:39][CH:38]=2)=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 31539964-((4-Methylpiperazin-1-yl)methyl)anilineHCID 86673368HCID 86673368, compound

Product 1

HCID 70683483HCID 70683483, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared according to synthesis procedure B described above from 2,5-dichloro-N-(4-fluoro-2-(pyrrolidin-1-ylsulfonyl)phenyl)pyrimidin-4-amine and 4-((4-methylpiperazin-1-yl)methyl)aniline in 78% yield (yellow solid) after flash chromatography (CH2Cl2/CH3OH 99:1 gradually increasing to 95:5). 1H NMR (400 MHz, CDCl3): δ 9.30 (s, 1H), 8.49 (dd, 1H, J=9.2, 4.8 Hz), 7.60 (dd, 1H, J=8.0, 2.9 Hz), 7.41 (d, 2H, J=8.2 Hz), 7.23 (d, 2H, J=8.2 Hz), 7.19 (m, 1H), 3.48 (s, 2H), 3.23 (m, 4H), 2.50 (bs, 8H), 2.31 (s, 3H), 1.78 (m, 4H); MS (ESI): 560.3 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-3d4959e995a6442bbc01a26d8177dad5
Source dataset
uspto-grants-2014_12
Patent number
US08901120B2

Reaction notes

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