Hydrochloric Acid → HCID 18670201, compound

HRID 1059418Notes

Reaction equation

HRID 1059418 reaction equation
C[Si](C)(C)[C:3]1[C:7]([C:8]2[CH:9]=[CH:10][C:11]3[S:16][C:15]4[N:17]=[CH:18][CH:19]=[N:20][C:14]=4[N:13]([CH2:21][O:22][CH3:23])[C:12]=3[CH:24]=2)=[CH:6][NH:5][N:4]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.Cl>O1CCCC1>[NH:5]1[CH:6]=[C:7]([C:8]2[CH:9]=[CH:10][C:11]3[S:16][C:15]4[N:17]=[CH:18][CH:19]=[N:20][C:14]=4[N:13]([CH2:21][O:22][CH3:23])[C:12]=3[CH:24]=2)[CH:3]=[N:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 178496765HCID 178496765, compound

Product 1

HCID 18670201HCID 18670201, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5 ml of a solution of 130 mg of 8-(3-trimethylsilyl-pyrazol-4-yl)-10-methoxymethyl-10H-pyrazino(2,3-b][1,4]-benzothiazine in tetrahydrofuran was stirred at room temperature and 1.1 ml of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran was added thereto. After stirring for 5 minutes, the reaction mixture was distributed into ethyl acetate and 1 N hydrochloric acid. The organic layer was extracted, washed with water and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 42 mg of the title compound as yellow crystals.

Workup

  1. extractionThe organic layer was extracted
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol)

Sources & evidence

ORD record
ord-12962dd019df4bb197cc2ba72c18d3f0
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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