Ammonia → 2-[4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy]acetamide

HRID 1271312Notes

Reaction equation

HRID 1271312 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][C:10]([N:19]([CH2:23][CH2:24][CH2:25][CH2:26][O:27][CH2:28][C:29](O)=[O:30])[CH:20]([CH3:22])[CH3:21])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:34](CC)CC)C.C(Cl)(=O)OCC.N>O1CCCC1>[C:1]1([C:7]2[N:8]=[CH:9][C:10]([N:19]([CH2:23][CH2:24][CH2:25][CH2:26][O:27][CH2:28][C:29]([NH2:34])=[O:30])[CH:20]([CH3:22])[CH3:21])=[N:11][C:12]=2[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 99318912-(4-((5,6-Diphenyl-2-pyrazinyl)(1-methylethyl)amino)butoxy)acetic acid

Product 1

HCID 184526472-[4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy]acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.50 g of 2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}acetic acid was dissolved in 20 ml of anhydrous tetrahydrofuran and 0.500 ml of triethylamine was added and then 0.376 ml of ethyl chlorocarbonate was added while stirring under ice cooling. After stirring under ice cooling for 45 minutes, a solution of saturated ammonia in 20 ml of tetrahydrofuran was added, followed by stirring for one hour. After removing an ice bath and stirring at room temperature for 18 hours, almost all of the solvent was evaporated. The residue was combined with water and then extracted with ethyl acetate. The extract was washed in turn with an aqueous saturated sodium hydrogen carbonate solution, 1N sodium hydroxide solution and water and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was washed with diethyl ether and then dried under reduced pressure to obtain 1.19 g of the desired product.

Workup

  1. stirringAfter stirring under ice cooling for 45 minutes
  2. stirringby stirring for one hour
  3. customAfter removing an ice bath
  4. stirringstirring at room temperature for 18 hours
  5. customalmost all of the solvent was evaporated
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed in turn with an aqueous saturated sodium hydrogen carbonate solution, 1N sodium hydroxide solution and water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. washThe residue was washed with diethyl ether
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-9bf55edc404744369bfa5f1d3bce82d7
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

Loading…