Ammonia → HCID 18670356, compound

HRID 1059433Notes

Reaction equation

HRID 1059433 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:9]2[CH:10]=[C:11]([C:14](O)=[O:15])[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[N:17]=[CH:18][CH:19]=[N:20][C:5]1=2.Cl.C([N:24]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.N.C(=O)(O)[O-].[Na+]>ClCCl.O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][CH2:3][N:4]1[C:9]2[CH:10]=[C:11]([C:14]([NH2:24])=[O:15])[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[N:17]=[CH:18][CH:19]=[N:20][C:5]1=2

Participants

9

Reactant 5

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11289238HCID 11289238, compound

Product 1

HCID 18670356HCID 18670356, compoundYield 59.8%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.04 g of (10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)carboxylic acid was dissolved in a mixture of dichloromethane (20 ml) with tetrahydrofuran (20 ml) in a nitrogen atmosphere. Under ice-cooling, 1.04 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 200 mg of 1-hydroxybenzotriazole were added thereto and the resulting mixture was stirred at room temperature for 30 minutes. After blowing ammonia gas thereinto, the reaction mixture was distributed into an aqueous solution of sodium bicarbonate and ethyl acetate. The organic layer was extracted, washed with water and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the crystals thus precipitated were filtered. Further, the aqueous layer was acidified and the starting materials were recovered. After repeating the above-mentioned procedures, the title compound (620 mg in total) was obtained as yellow crystals.

Workup

  1. temperatureUnder ice-cooling
  2. extractionThe organic layer was extracted
  3. washwashed 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. filtrationwere filtered
  8. customthe starting materials were recovered

Sources & evidence

ORD record
ord-9f524b1848244b9b9f3c5c12454f79c0
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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