Lithium Chloride → HCID 20463835, compound

HRID 325607Notes

Reaction equation

HRID 325607 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:15](OC)=[O:16])[C:5]([NH:9][CH2:10][C:11](OC)=[O:12])=[N:6][C:7]=1[Cl:8].[BH4-].[K+].[Cl-].[Li+].P([O-])(O)(O)=O.[K+]>O1CCCC1.ClCCl.O>[Cl:1][C:2]1[N:3]=[C:4]([CH2:15][OH:16])[C:5]([NH:9][CH2:10][CH2:11][OH:12])=[N:6][C:7]=1[Cl:8]

Participants

8

Reactant 4

HCID 433294Lithium Chloride2×HCID 516951Monobasic potassium phosphateHCID 4192641Potassium borohydride2×HCID 53926692HCID 53926692, compound

Product 1

HCID 20463835HCID 20463835, compoundYield 79.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 2.5 ml of tetrahydrofuran there was dissolved methyl [(5,6-dichloro-3-(methoxycarbonyl)pyrazinyl)amino]acetate (50 mg), prepared as in Step B above, after which potassium borohydride (22 mg; 0.0012 Mol) and lithium chloride (18 mg) were added. The reaction mixture was stirred overnight at room temperature. An additional 44 mg of potassium borohydride and 36 mg of lithium chloride were then added, and the reaction mixture was stirred at room temperature for 6 hours. Water (1 ml) was added, and the reaction mixture was cooled and stirred for 15 minutes, after which potassium dihydrogen phosphate (653 mg; 0.0048 Mol) was added. The solvent was blown off under nitrogen, and the residue was taken up in dichloromethane and filtered. The precipitate was washed twice with dichloromethane and once with ethyl acetate. The combined filtrates were concentrated under vacuum to give the title compound (32 mg).

Workup

  1. additionwere added
  2. stirringthe reaction mixture was stirred at room temperature for 6 hours
  3. temperaturethe reaction mixture was cooled
  4. stirringstirred for 15 minutes
  5. filtrationfiltered
  6. washThe precipitate was washed twice with dichloromethane and once with ethyl acetate
  7. concentrationThe combined filtrates were concentrated under vacuum

Sources & evidence

ORD record
ord-3a2efedd27fa4a5ea8d0a21dcc362807
Source dataset
uspto-grants-1984_04
Patent number
US04442097

Reaction notes

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