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

HRID 883685Notes

Reaction equation

HRID 883685 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[NH:19][CH2:20][CH2:21][CH2:22][N:23]([CH3:32])[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)[C:5]([N:7]([CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:8][CH:9]([CH3:11])[CH3:10])=[O:6].[C:33](N1C=CN=C1)(N1C=CN=C1)=[S:34]>C1COCC1.ClCCl.O>[CH2:12]([N:7]([CH2:8][CH:9]([CH3:11])[CH3:10])[C:5]([C:4]1[CH:16]=[CH:17][C:18]2[N:19]([CH2:20][CH2:21][CH2:22][N:23]([CH3:32])[CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[C:33](=[S:34])[NH:1][C:2]=2[CH:3]=1)=[O:6])[CH:13]([CH3:14])[CH3:15]

Participants

6

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 690267883-amino-N,N-diisobutyl-4-({3-[methyl(2-pyridin-2-ylethyl)amino]propyl}amino)benzamide

Product 1

HCID 86596757N,N-diisobutyl-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-2-thioxo-2,3-dihydro-1H-benzimidazole-5-carboxamideYield 72%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 3-amino-N,N-diisobutyl-4-({3-[methyl(2-pyridin-2-ylethyl)amino]propyl}amino) benzamide (1.52 g, 1 eq) and thiocarbonyldiimidazole (0.74 g, 1.2 eq) in THF (30 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 (80 ml) and water (30 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 of the residue by flash chromatography on silica gel (eluent: 100% dichloromethane to dichloromethane/methanol 8:2) produces the expected compound in the form of a light beige foam (1.2 g; 72% 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 of the residue by flash chromatography on silica gel (eluent: 100% dichloromethane to dichloromethane/methanol 8:2)

Sources & evidence

ORD record
ord-6bdfe502bbe44bb1a50e70c5e4d110aa
Source dataset
uspto-grants-2012_08
Patent number
US08236965B2

Reaction notes

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