1,1'-Thiocarbonyldiimidazole → methyl 1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-2-thioxo-2,3-dihydro-1H-benzimidazole-5-carboxylate

HRID 1727418Notes

Reaction equation

HRID 1727418 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

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 69027376Methyl 3-amino-4-({3-[methyl(2-pyridin-2-ylethyl)amino]propyl}amino)benzoate

Product 1

HCID 86596758methyl 1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-2-thioxo-2,3-dihydro-1H-benzimidazole-5-carboxylateYield 85%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

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

  1. concentrationAfter concentration under reduced pressure at 40° C.
  2. customthe residue obtained
  3. customAfter decanting
  4. extractionextracting
  5. washthe combined organic phases are washed with salt water
  6. dry with materialdried over Na2SO4
  7. customthen evaporated under reduced pressure at 40° C
  8. customPurification by flash chromatography on silica gel (eluent: 100% dichloromethane to dichloromethane/methanol 9:1)

Sources & evidence

ORD record
ord-167a6b95698a4c6187425b392d2917b9
Source dataset
uspto-grants-2009_02
Patent number
US07495110B2

Reaction notes

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