Toluene → HCID 22709521, compound

HRID 352975Notes

Reaction equation

HRID 352975 reaction equation
[C:1]([CH:4]1[CH2:9][N:8]([S:10]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([Cl:23])[CH:19]=3)[CH:14]=2)(=[O:12])=[O:11])[CH2:7][CH2:6][N:5]1[C:24]([C:26]1[S:27][C:28]2[CH2:33]C(C)N[CH2:30][C:29]=2[N:35]=1)=[O:25])(=[O:3])[NH2:2].[C:36]1([CH3:42])C=CC=CC=1.C[Si]([N-:47][Si](C)(C)C)(C)C.[K+].[CH3:53][S:54](Cl)(=[O:56])=[O:55]>O1CCCC1.Cl>[ClH:23].[Cl:23][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13]([S:10]([N:8]1[CH2:7][CH2:6][N:5]([C:24]([C:26]3[S:27][C:28]4[CH2:33][NH:47][CH:36]([CH3:42])[CH2:30][C:29]=4[N:35]=3)=[O:25])[CH:4]([C:1]([NH:2][S:54]([CH3:53])(=[O:56])=[O:55])=[O:3])[CH2:9]1)(=[O:12])=[O:11])[CH:22]=[CH:21]2

Participants

7

Reactant 4

HCID 1140TolueneHCID 31297Methanesulfonyl chlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 22710834HCID 22710834, compound

Product 1

HCID 22709521HCID 22709521, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (30 ml) was dissolved 2-carbamoyl-4-[(6-chloronaphthalen-2-yl)sulfonyl]-1-[(6-methyl-4,5,6,7-tetrahydrothiazolo[4,5-c]pyridin-2-yl)carbonyl]piperazine (300 mg), followed by the addition of a 0.5 mole toluene solution (1.12 ml) of potassium bis(trimethylsilyl)amide. The resulting mixture was stirred for 10 minutes under ice cooling. After the addition of methanesulfonyl chloride (0.04 ml), the resulting mixture was warmed up to room temperature and stirred for 1 hour. The reaction mixture was concentrated under reduced pressure. Methylene chloride was added to the residue and the resulting mixture was washed once with water and once with saturated aqueous NaCl solution. The organic layer thus extracted was dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (methylene chloride:methanol=100:0→100:3), whereby colorless foam was obtained. The resulting foam was suspended in 1N hydrochloric acid (1 ml). The resulting suspension was concentrated under reduced pressure, whereby the title compound (96 mg) was obtained as pale yellow foam.

Workup

  1. stirringstirred for 1 hour
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionMethylene chloride was added to the residue
  4. washthe resulting mixture was washed once with water and once with saturated aqueous NaCl solution
  5. extractionThe organic layer thus extracted
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. distillationdistilled under reduced pressure
  8. customto remove the solvent
  9. customThe residue was purified by chromatography on a silica gel column (methylene chloride:methanol=100:0→100:3), whereby colorless foam
  10. customwas obtained
  11. concentrationThe resulting suspension was concentrated under reduced pressure, whereby the title compound (96 mg)
  12. customwas obtained as pale yellow foam

Sources & evidence

ORD record
ord-9e7f25dc528d4a449237aa1cb76256cc
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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