1,1'-Thiocarbonyldiimidazole → methyl 1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-2-thioxo-2,3-dihydro-1H-benzimidazole-5-carboxylate
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[NH:12][CH2:13][CH2:14][CH2:15][N:16]([CH3:25])[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)[C:5]([O:7][CH3:8])=[O:6].[C:26](N1C=CN=C1)(N1C=CN=C1)=[S:27]>O1CCCC1.ClCCl.O>[CH3:25][N:16]([CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)[CH2:15][CH2:14][CH2:13][N:12]1[C:11]2[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=2[NH:1][C:26]1=[S:27]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 20 °C
Procedure
A mixture of methyl 3-amino-4-({3-[methyl(2-pyridin-2-ylethyl)amino]propyl}amino)benzoate (4.09 g, 1 eq) and thiocarbonyldiimidazole (2.77 g, 1.3 eq) in tetrahydrofuran (100 ml) is stirred at approximately 20° C. for 15 hours. After concentration under reduced pressure at 40° C., the residue obtained is taken up in dichloromethane (150 ml) and water (50 ml). After decanting and extracting, the combined organic phases are washed with salt water, dried over Na2SO4 then evaporated under reduced pressure at 40° C. Purification by flash chromatography on silica gel (eluent: 100% dichloromethane to dichloromethane/methanol 9:1) produces the expected compound in the form of a foam (3.94 g; 85% yield).
Workup
- concentrationAfter concentration under reduced pressure at 40° C.
- customthe residue obtained
- customAfter decanting
- extractionextracting
- washthe combined organic phases are washed with salt water
- dry with materialdried over Na2SO4
- customthen evaporated under reduced pressure at 40° C
- customPurification by flash chromatography on silica gel (eluent: 100% dichloromethane to dichloromethane/methanol 9:1)
Sources & evidence
- ORD record
- ord-ca8d0970b2c549e3ba4f24254994c3da
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08236965B2
Reaction notes
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