1-(3-Aminopropyl)-4-methylpiperazine → (2-{2-[3-(4-Methylpiperazin-1-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophen-6-ylmethyl)-carbamic acid tert-butyl ester

HRID 1986192

Reaction equation

HRID 1986192 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]2[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][N:20]=[C:19](Cl)[N:18]=3)[S:14][C:13]=2[CH:24]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:26][CH2:27][CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]1>O1CCOCC1>[C:1]([O:5][C:6](=[O:25])[NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]2[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:26][CH2:27][CH2:28][CH2:29][N:30]4[CH2:31][CH2:32][N:33]([CH3:36])[CH2:34][CH2:35]4)[N:18]=3)[S:14][C:13]=2[CH:24]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 783281-(3-Aminopropyl)-4-methylpiperazineHCID 86625348[2-(2-Chloropyrimidin-4-yl)-benzo[b]thiophen-6-ylmethyl]-carbamic acid tert-butyl ester

Product 1

HCID 68859103(2-{2-[3-(4-Methylpiperazin-1-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophen-6-ylmethyl)-carbamic acid tert-butyl esterYield 70.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of [2-(2-chloropyrimidin-4-yl)-benzo[b]thiophen-6-ylmethyl]-carbamic acid tert-butyl ester (1.47 g, 3.90 mmol) and 1-(3-aminopropyl)-4-methylpiperazine (1.36 g, 8.60 mmol) in dioxane (38 mL) is refluxed for 3 hours. The solvent is removed and the residue is subjected to chromatography on silica gel, eluting with 2.0 M NH3/MeOH in CHCl3 0-10%, to obtain the title compound (1.36 g, 70% yield). ES+(m/z) 497 [M+H].

Workup

  1. temperatureis refluxed for 3 hours
  2. customThe solvent is removed
  3. washeluting with 2.0 M NH3/MeOH in CHCl3 0-10%

Sources & evidence

ORD record
ord-09c30005acbf4e2d84c146f67df2fb9b
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Linked notes

Loading…