Dichloromethane → HCID 23564544, compound

HRID 1059421Notes

Reaction equation

HRID 1059421 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][CH2:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]2[S:19][C:18]3[N:20]=[CH:21][CH:22]=[N:23][C:17]=3[N:16](COC)[C:15]=2[CH:27]=1)=O.S(Cl)(Cl)=O.ClCCl>C(Cl)(Cl)(Cl)Cl>[N:7]1[CH:8]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]3[S:19][C:18]4[N:20]=[CH:21][CH:22]=[N:23][C:17]=4[NH:16][C:15]=3[CH:27]=2)[N:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=12

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 23565187[N-(2-Pyridyl)aminometyl](10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)ketone

Product 1

HCID 23564544HCID 23564544, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

10 ml of a solution of 200 mg of [N-(2-pyridyl)aminometyl](10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)ketone in carbon tetrachloride was stirred at room temperature and 240 mg of thionyl chloride was dropped thereinto. The reaction mixture was distributed into dichloromethane and an aqueous solution of sodium bicarbonate and the organic layer was separated. To the organic layer were added methanol and tetrahydrofuran to give a homogeneous solution. After adding silica gel and distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 103 mg of the title compound as yellow crystals.

Workup

  1. customan aqueous solution of sodium bicarbonate and the organic layer was separated
  2. additionTo the organic layer were added methanol and tetrahydrofuran
  3. customto give a homogeneous solution
  4. additionAfter adding silica gel
  5. distillationdistilling off the solvent under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol)

Sources & evidence

ORD record
ord-ce1339966b1f4c70899cfbbe10757b5f
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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