Hydrochloric Acid → HCID 57663900, compound

HRID 1510250Notes

Reaction equation

HRID 1510250 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]([CH2:13][C:14](=[O:28])[NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.[BH4-].[Na+].O.Cl>CO.O1CCCC1>[OH:3][CH2:4][CH2:5][N:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:13][C:14]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)=[O:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 131729801HCID 131729801, compound

Product 1

HCID 57663900HCID 57663900, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Ethyl[(2-oxo-2-{[4-(4-pyridinyl)phenyl]amino}ethyl) (phenyl)amino]acetate (50.0 mg) was dissolved in methanol/tetrahydrofuran (1:1, 1.0 mL) and sodium borohydride (14.6 mg) was added portionwise to the mixture cooled with ice bath stirring. The mixture was stirred at 0° C. for 5 hours and water (2.0 mL) was added to the resulting mixture. The mixture was neutralized with 1N hydrochloric acid and extracted with ethyl acetate (3.0 mL). The organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by silica gel column chromatography (2 g, 10% methanol in chloroform) to afford 2-[(2-hydroxyethyl) (phenyl)amino]-N-[4-(4-pyridinyl)phenyl]acetamide (21.4 mg) as white crystals.

Workup

  1. temperaturecooled with ice bath
  2. stirringThe mixture was stirred at 0° C. for 5 hours
  3. extractionextracted with ethyl acetate (3.0 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated in vacuo
  7. customthe residue was purified by silica gel column chromatography (2 g, 10% methanol in chloroform)

Sources & evidence

ORD record
ord-e85310c511b84bdc826b397f74f8825e
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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