Sodium borohydride → HCID 86757594, compound

HRID 429688Notes

Reaction equation

HRID 429688 reaction equation
CO[C:3]1[C:4]([N:53]=[C:54]=[O:55])=[C:5]([CH:32]=[CH:33][C:34]=1C1C2N=C(CNC(OC(C)(C)C)=O)NC=2C=CC=1)[C:6]([N:8](C)C1C=CC(C)=CC=1OCCCCCC(N1CCC(=O)CC1)=O)=[O:7].[BH4-].[Na+]>CO.C(Cl)(Cl)Cl>[C:54](=[N:53][C:4]1[CH:3]=[CH:34][CH:33]=[CH:32][C:5]=1[C:6]([NH2:8])=[O:7])=[O:55]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86757595HCID 86757595, compound

Product 1

HCID 86757594HCID 86757594, compoundYield 464.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-oxopiperidin-1-yl)carbonylpent-1-yloxy]phenyl]-4-[2-(tert-butoxycarbonyl)aminomethyl-1H-benzimidazol-4-yl]-carbonylaminobenzamide (150 mg) in methanol (5 ml) was added sodium borohydride (7.52 mg) under an ice bath cooling and the mixture was stirred at the same temperature for 1 hour. The mixture was diluted with chloroform and the solution was washed with water and brine. The organic phase was dried over magnesium sulfate and the solvent was evaporated in vacuo to give N-[2-[5-(4-hydroxypiperidin-1-yl)carbonylpent-1-yloxy]-4-methylphenyl]-3-methoxy-N-methyl-4-[2-tert-butoxycarbonyl)aminomethyl-1H-benzimidazol-4-yl]carbonylaminobenzamide (150 mg).

Workup

  1. temperaturecooling
  2. washthe solution was washed with water and brine
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-eefa20fac9144a40b448469307f83df7
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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