Sodium borohydride → 2-{[2-hydroxy-2-(3,4,5-trimethoxyphenyl)ethyl]thio}-N,N-diisobutyl-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-1H-benzimidazole-5-carboxamide

HRID 883701Notes

Reaction equation

HRID 883701 reaction equation
[BH4-].[Na+].[CH2:3]([N:7]([CH2:48][CH:49]([CH3:51])[CH3:50])[C:8]([C:10]1[CH:47]=[CH:46][C:13]2[N:14]([CH2:33][CH2:34][CH2:35][N:36]([CH3:45])[CH2:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=3)[C:15]([S:17][CH2:18][C:19](=[O:32])[C:20]3[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=3)=[N:16][C:12]=2[CH:11]=1)=[O:9])[CH:4]([CH3:6])[CH3:5]>CO>[OH:32][CH:19]([C:20]1[CH:21]=[C:22]([O:30][CH3:31])[C:23]([O:28][CH3:29])=[C:24]([O:26][CH3:27])[CH:25]=1)[CH2:18][S:17][C:15]1[N:14]([CH2:33][CH2:34][CH2:35][N:36]([CH3:45])[CH2:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=2)[C:13]2[CH:46]=[CH:47][C:10]([C:8]([N:7]([CH2:48][CH:49]([CH3:51])[CH3:50])[CH2:3][CH:4]([CH3:5])[CH3:6])=[O:9])=[CH:11][C:12]=2[N:16]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57567654N,N-diisobutyl-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-2-{[2-oxo-2-(3,4,5-trimethoxyphenyl)ethyl]thio}-1H-benzimidazole-5-carboxamide

Product 1

HCID 575676302-{[2-hydroxy-2-(3,4,5-trimethoxyphenyl)ethyl]thio}-N,N-diisobutyl-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-1H-benzimidazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (8 mg, 2 eq) is added at 0° C. to a solution of N,N-diisobutyl-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-2-{[2-oxo-2-(3,4,5-trimethoxyphenyl)ethyl]thio}-1H-benzimidazole-5-carboxamide (69 mg, 1 eq) in methanol (2 ml). After stirring for 10 minutes at 0° C., the mixture is taken to a temperature of approximately 20° C. and stirred at this temperature for 30 minutes. The mixture is then concentrated under reduced pressure at 40° C. then water saturated with ammonium chloride and dichloromethane is added. After decanting and extracting, the organic phases are combined and washed with salt water, dried over sodium sulphate and evaporated under reduced pressure at 40° C. Purification of the oil obtained by flash chromatography on silica gel (100% dichloromethane to dichloromethane/methanol 80:20) produces the expected compound in the form of an oil (61 mg, 88% yield).

Workup

  1. customis taken to a temperature of approximately 20° C.
  2. stirringstirred at this temperature for 30 minutes
  3. concentrationThe mixture is then concentrated under reduced pressure at 40° C.
  4. additionwater saturated with ammonium chloride and dichloromethane is added
  5. customAfter decanting
  6. extractionextracting
  7. washwashed with salt water
  8. dry with materialdried over sodium sulphate
  9. customevaporated under reduced pressure at 40° C
  10. customPurification of the oil
  11. customobtained by flash chromatography on silica gel (100% dichloromethane to dichloromethane/methanol 80:20)

Sources & evidence

ORD record
ord-f4662b6ef9f3456e89880723d25c9b19
Source dataset
uspto-grants-2012_08
Patent number
US08236965B2

Reaction notes

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