Water → HCID 118598606, compound

HRID 1050393Notes

Reaction equation

HRID 1050393 reaction equation
COC1C=CC(C[S:8][C:9]2[C:14](=[O:15])[N:13]3[C:16]4([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)[NH:17][C:18](=[O:19])[C:12]3=[C:11]([CH3:25])[CH:10]=2)=CC=1.CS(O)(=O)=O.O>C(Cl)(Cl)Cl>[SH:8][C:9]1[C:14](=[O:15])[N:13]2[C:16]3([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[NH:17][C:18](=[O:19])[C:12]2=[C:11]([CH3:25])[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 118598780HCID 118598780, compound

Product 1

HCID 118598606HCID 118598606, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 6′-((4-methoxybenzyl)thio)-8′-methyl-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione (3, 3.3 g, 8.58 mmol) in chloroform (40 mL) is added methanesulfonic acid (3 mL, 46.23 mmol). The reaction is stirred at 50° C. overnight. The resulting mixture is cooled to room temperature, poured into water and extracted with dichloromethane. The organic layer is dried over magnesium sulfate, filtered and concentrated. The crude is purified via column chromatography to afford 6′-mercapto-8′-methyl-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione (4).

Workup

  1. temperatureThe resulting mixture is cooled to room temperature
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude is purified via column chromatography

Sources & evidence

ORD record
ord-4b3c4725745b467eb8df9444d79a434f
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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