(R)-2-Chloro-3-(2-methylpiperazin-1-YL)pyrazine → 2-{2-[{2-[(1E)-3-(Dimethylamino)prop-1-enyl]pyridin-3-yl}oxy]ethoxy}-3-[(2R)-2-methylpiperazin-1-yl]pyrazine

HRID 1765089Notes

Reaction equation

HRID 1765089 reaction equation
Cl[C:2]1[C:7]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]2[CH3:14])=[N:6][CH:5]=[CH:4][N:3]=1.[CH3:15][N:16]([CH3:30])[CH2:17]/[CH:18]=[CH:19]/[C:20]1[C:25]([O:26][CH2:27][CH2:28][OH:29])=[CH:24][CH:23]=[CH:22][N:21]=1>>[CH3:30][N:16]([CH3:15])[CH2:17]/[CH:18]=[CH:19]/[C:20]1[C:25]([O:26][CH2:27][CH2:28][O:29][C:2]2[C:7]([N:8]3[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]3[CH3:14])=[N:6][CH:5]=[CH:4][N:3]=2)=[CH:24][CH:23]=[CH:22][N:21]=1

Participants

3

Reactant 2

HCID 9992195(R)-2-Chloro-3-(2-methylpiperazin-1-YL)pyrazineHCID 211066492-({2-[(1E)-3-(Dimethylamino)prop-1-enyl]pyridin-3-yl}oxy)ethanol

Product 1

HCID 100009382-{2-[{2-[(1E)-3-(Dimethylamino)prop-1-enyl]pyridin-3-yl}oxy]ethoxy}-3-[(2R)-2-methylpiperazin-1-yl]pyrazineYield 5.5%

Procedure

The procedure in Example 18, Step 4, was followed starting from 2-chloro-3-[(2R)-2-methylpiperazin-1-yl]pyrazine* (0.30 g, 1.4 mmol) and 2-({2-[(1E)-3-(dimethylamino)prop-1-enyl]pyridin-3-yl}oxy)ethanol (from Step 2; 0.32 g, 1.5 mmol). The crude product was purified on a column of silica (100 mm, i.d.=30 mm) with CHCl3/MeOH/NH4OH (80:20:0.5; 200 mL, followed by 60:40:1) as eluent to give 0.030 g (5.5%) of the title compound as a light brown oil. HRMS m/z calcd for C21H30N6O2 (M)+ 398.2430. found 398.2433. *Reported in WO 00/76984, Example 192, Step 2.

Workup

  1. customThe crude product was purified on a column of silica (100 mm, i.d.=30 mm) with CHCl3/MeOH/NH4OH (80:20:0.5; 200 mL, followed by 60:40:1) as eluent

Sources & evidence

ORD record
ord-6f268947c27f444d8fe0aafc68a667e1
Source dataset
uspto-grants-2007_06
Patent number
US07226925B2

Reaction notes

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