Water → HCID 59936433, compound

HRID 567866Notes

Reaction equation

HRID 567866 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH2:11][CH2:10][CH2:9][C@@H:8]2[CH2:12][NH2:13])[CH2:3][CH2:2]1.[Cl:14][C:15]1[N:20]=[C:19](Cl)[C:18](=[O:22])[N:17]([CH2:23][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[C:16]=1[CH3:34].C(N(CC)CC)C.O>C(OCC)(=O)C>[Cl:14][C:15]1[N:20]=[C:19]([NH:13][CH2:12][C@H:8]2[CH2:9][CH2:10][CH2:11][N:7]2[CH:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)[C:18](=[O:22])[N:17]([CH2:23][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[C:16]=1[CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10663926Benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetateHCID 59936441HCID 59936441, compound

Product 1

HCID 59936433HCID 59936433, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of [(2R)-1-tetrahydro-2H-pyran-4-yl-2-pyrrolidinyl]methylamine (preparation 157) (460 mg, 2.50 mmol), benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetate (preparation 17), and triethylamine (870 ml, 6.24 mmol) in ethyl acetate (8 ml) was heated under reflux for 18 hrs, then cooled. Water (1.5 ml) was added, the reaction mixture dried over MgSO4, and filtered through celite, washing the filter pad well with ethyl acetate. The combined filtrates were concentrated under reduced pressure and the residue purified by column chromatography on silica gel using hexane:ethyl acetate (50:50) as eluant to give the desired product as a white solid, (970 mg, 82%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hrs
  3. temperaturecooled
  4. dry with materialthe reaction mixture dried over MgSO4
  5. filtrationfiltered through celite
  6. washwashing the filter pad well with ethyl acetate
  7. concentrationThe combined filtrates were concentrated under reduced pressure
  8. customthe residue purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-dd3af7deb659469082b734e32856dd33
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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