Ammonia → HCID 69885766, compound

HRID 1059434Notes

Reaction equation

HRID 1059434 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:9]2[CH:10]=[C:11](/[CH:14]=[CH:15]/[C:16](O)=[O:17])[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[N:19]=[CH:20][CH:21]=[N:22][C:5]1=2.ClP(=O)(OCC)OCC.[NH3:32].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][CH2:3][N:4]1[C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][C:16]([NH2:32])=[O:17])[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[N:19]=[CH:20][CH:21]=[N:22][C:5]1=2

Participants

8

Reactant 4

HCID 222AmmoniaHCID 10340Sodium CarbonateHCID 13139Diethyl chlorophosphateHCID 18670105HCID 18670105, compound

Product 1

HCID 69885766HCID 69885766, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

950 mg of (E)-3-(10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)propenoic acid was dissolved in a solvent mixture of tetrahydrofuran (10 ml) with N,N-dimethylformamide (10 ml) in a nitrogen atmosphere. Under ice-cooling, 0.48 ml of diethyl chlorophosphonate was dropped into the reaction mixture. After stirring at room temperature for 30 minutes, ammonia gas was blown into the system. Then the reaction mixture was distributed into an aqueous solution of sodium carbonate and ethyl acetate and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the crystals thus precipitated were recrystallized from diisopropyl ether/ethyl acetate to thereby give 400 mg of the title compound as yellow crystals.

Workup

  1. temperatureUnder ice-cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationAfter distilling off the solvent under reduced pressure
  6. customthe crystals thus precipitated
  7. customwere recrystallized from diisopropyl ether/ethyl acetate

Sources & evidence

ORD record
ord-1b08e55887de4987b1de187c8125adfc
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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