Pyridine → 5-Bis(methanesulfonyl)amino-6-(2-thiazolylthio)-1-indanone

HRID 1654785Notes

Reaction equation

HRID 1654785 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].N1C=CC=CC=1.[NH2:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][C:21]=1[S:22][C:23]1[S:24][CH:25]=[CH:26][N:27]=1)[C:18](=[O:28])[CH2:17][CH2:16]2.CCN(CC)CC>C(Cl)Cl.O>[CH3:1][S:2]([N:12]([S:2]([CH3:1])(=[O:4])=[O:3])[C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][C:21]=1[S:22][C:23]1[S:24][CH:25]=[CH:26][N:27]=1)[C:18](=[O:28])[CH2:17][CH2:16]2)(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 105634525-Amino-6-(2-thiazolylthio)-1-indanone

Product 1

HCID 107644915-Bis(methanesulfonyl)amino-6-(2-thiazolylthio)-1-indanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonyl chloride (710 μL, 9.15 mmol) and pyridine (740 μL, 9.15 mmol) were added to a solution of the aminoindanone from Step 8 in CH2Cl2 (5 mL). After stirring overnight at room temperature, Et3N (400 μL, 2.8 mmol) and methanesulfonyl chloride (220 μL, 2.8 mmol) were added. The mixture was stirred 4 h at room temperature. Water and CH2Cl2 were added, the aqueous phase was extracted with CH2Cl2 and the combined organic phase was washed with 0.1M aqueous citric acid, dried over MgSO4 and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel (20% EtOAc in CHCl2) to give 175 mg of the title compound.

Workup

  1. stirringThe mixture was stirred 4 h at room temperature
  2. extractionthe aqueous phase was extracted with CH2Cl2
  3. washthe combined organic phase was washed with 0.1M aqueous citric acid
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by flash chromatography on silica gel (20% EtOAc in CHCl2)

Sources & evidence

ORD record
ord-b2fc9bfd70ed4826a587021d82eb17ea
Source dataset
uspto-grants-1995_04
Patent number
US05409944

Reaction notes

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