Hydrochloric Acid → HCID 69103555, compound

HRID 2217248Notes

Reaction equation

HRID 2217248 reaction equation
[C:1]([C:4]1[N:9]=[C:8]([C:10]2[CH:11]=[CH:12][C:13](=[O:19])[N:14]([CH:16]([CH3:18])[CH3:17])[CH:15]=2)[C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:6][C:5]=1[NH2:26])(=[O:3])[CH3:2].[BH4-].[Na+].Cl.O>C1COCC1.CO.CCOC(C)=O>[NH2:26][C:5]1[N:6]=[C:7]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:8]([C:10]2[CH:11]=[CH:12][C:13](=[O:19])[N:14]([CH:16]([CH3:17])[CH3:18])[CH:15]=2)=[N:9][C:4]=1[CH:1]([OH:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 69103232HCID 69103232, compound

Product 1

HCID 69103555HCID 69103555, compoundYield 19.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 5-(6-acetyl-5-amino-3-phenyl-2-pyrazinyl)-1-isopropyl-2(1H)-pyridone (82 mg) in THF-MeOH (1:1, 2.0 ml), was added sodium borohydride (8.9 mg). The mixture was stirred st room temperature for 4 hours. 1N HCl (0.05 ml) was poured into the mixtre. Water and EtOAc were poured into the mixture and the organic layer was separated, washed with water and brine, and dried over MgSO4. The solvent was removed under reduced pressure. The residue was purified by column chromatography. The desired product was recrystallized from EtOH and dried in vacuo to give 5-[5-amino-6-(1-hydroxyethyl)-3-phenyl-2-pyrazinyl]-1-isopropyl-2(1H)-pyridone (16 mg).

Workup

  1. customthe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography
  6. customThe desired product was recrystallized from EtOH
  7. customdried in vacuo

Sources & evidence

ORD record
ord-fbe59a2f466b4fd9ab317aa711a07020
Source dataset
uspto-grants-2008_08
Patent number
US07407961B2

Reaction notes

Loading…