Triethylamine → HCID 44216363, compound

HRID 2217239Notes

Reaction equation

HRID 2217239 reaction equation
[NH2:1][C:2]1[C:3]([C:24](O)=[O:25])=[N:4][C:5]([C:14]2[CH:19]=[CH:18][C:17](=[O:20])[N:16]([CH:21]([CH3:23])[CH3:22])[CH:15]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.CCN(CC)CC.ClC(OCC(C)C)=O.[BH4-].[Na+]>C1COCC1.O.CCOC(C)=O>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]([C:14]2[CH:19]=[CH:18][C:17](=[O:20])[N:16]([CH:21]([CH3:23])[CH3:22])[CH:15]=2)=[N:4][C:3]=1[CH2:24][OH:25]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 69103454HCID 69103454, compound

Product 1

HCID 44216363HCID 44216363, compoundYield 35.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridyl)-5-phenyl-2-pyrazinecarboxylic acid (70 mg) and NEt3 (40.4 mg) in THF (0.7 ml), was added isobutyl chloroformate (32.7 mg) under ice-bath cooling. After 1.5 hours stirring at the same temperature, the mixture was poured into a mixture of sodium borohydride (30.2 mg) in a mixture of THF (0.7 ml) and water (1.4 ml) under ice-bath cooling. After 2.5 hours stirring at the same temperature, the mixture was diluted with water and EtOAc, and then 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 silica-gel column chromatography (CH2:Cl2:MeOH=25:1-10:1). A desired fraction was triturated with IPE to give 5-[5-amino-6-(hydroxymethyl)-3-phenyl-2-pyrazinyl]-1-isopropyl-2(1H)-pyridone (24 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringAfter 2.5 hours stirring at the same temperature
  4. customthe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed under reduced pressure
  8. customThe residue was purified by silica-gel column chromatography (CH2:Cl2:MeOH=25:1-10:1)
  9. customA desired fraction was triturated with IPE

Sources & evidence

ORD record
ord-5469a49e0e9440da8ef5f8c019b6b4aa
Source dataset
uspto-grants-2008_08
Patent number
US07407961B2

Reaction notes

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