Formic Acid → HCID 18670546, compound

HRID 1059435Notes

Reaction equation

HRID 1059435 reaction equation
Cl[S:2]([N:5]=C=O)(=[O:4])=[O:3].C(O)=O.[NH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]2[S:21][C:20]3[N:22]=[CH:23][CH:24]=[N:25][C:19]=3[NH:18][C:17]=2[CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)(=O)C>[N:25]1[C:19]2[NH:18][C:17]3[CH:26]=[C:13]([CH2:12][NH:11][S:2]([NH2:5])(=[O:4])=[O:3])[CH:14]=[CH:15][C:16]=3[S:21][C:20]=2[N:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 284Formic AcidHCID 11430Potassium CarbonateHCID 70918Chlorosulfonyl isocyanateHCID 18670209HCID 18670209, compound

Product 1

HCID 18670546HCID 18670546, compoundYield 12.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

5 ml of a solution of 283 mg of chlorosulfonyl isocyanate in tetrahydrofuran was ice-cooled and 92 mg of formic acid was added thereto. After stirring at room temperature for 30 minutes, the mixture was added to a solution of 276 mg of 8-aminomethyl-10H-pyrazino[2,3-b][1,4]benzothiazine in tetrahydrofuran (5 ml) and the resulting mixture was stirred at room temperature for 20 minutes. Next, it was distributed into an aqueous solution of potassium carbonate and ethyl acetate and the aqueous layer was extracted. The aqueous layer was well washed with ethyl acetate and the organic solvent contained therein was distilled off under reduced pressure. The residual aqueous solution was purified by High-porous gel chromatography (CHP20P mfd. by Mitsubishi Chemical Industries, Ltd., 75-150 μ) (eluted with water/methanol) to thereby give 45 mg of the title compound as yellow crystals.

Workup

  1. temperaturecooled
  2. stirringthe resulting mixture was stirred at room temperature for 20 minutes
  3. extractionthe aqueous layer was extracted
  4. washThe aqueous layer was well washed with ethyl acetate
  5. distillationthe organic solvent contained therein was distilled off under reduced pressure
  6. customThe residual aqueous solution was purified by High-porous gel chromatography (CHP20P mfd. by Mitsubishi Chemical Industries, Ltd., 75-150 μ) (eluted with water/methanol)

Sources & evidence

ORD record
ord-6d277bd5f66d4f6ea76872ac55089212
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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