Cesium carbonate → HCID 118598780, compound

HRID 1050413Notes

Reaction equation

HRID 1050413 reaction equation
Cl[C:2]1[CH:7]=[C:6](NC2N=CN=C(NC(C3CC3)=O)C=2)[C:5](=[O:21])[N:4]2[C:22]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29](F)C=3)(C)[NH:23][C:24](=[O:25])[C:3]=12.[C:34](=O)([O-])[O-].[Cs+].[Cs+].[CH3:40][O:41][C:42]1[CH:47]=[CH:46][C:45]([CH2:48][SH:49])=[CH:44][CH:43]=1>CC(O)C>[CH3:40][O:41][C:42]1[CH:47]=[CH:46][C:45]([CH2:48][S:49][C:6]2[C:5](=[O:21])[N:4]3[C:22]4([CH2:27][CH2:32][CH2:31][CH2:30][CH2:29]4)[NH:23][C:24](=[O:25])[C:3]3=[C:2]([CH3:34])[CH:7]=2)=[CH:44][CH:43]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 804074-Methoxy-alpha-toluenethiolHCID 118598561HCID 118598561, compound

Product 1

HCID 118598780HCID 118598780, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

6′-Bromo-8′-methyl-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione (1, 2.0 g, 6.42 mmol) was dissolved in 2-propanol (20 mL). To this mixture was added cesium carbonate (6.28 g, 19.28 mmol), followed by (4-methoxyphenyl)methanethiol (1.18 g, 7.71 mmol). The reaction mixture was stirred at 70° C. for 16 h. After completion, solvent was evaporated under reduced pressure and the crude was washed with water (50 mL) followed by diethyl ether and then dried under reduced pressure to afford 6′-((4-methoxybenzyl)thio)-8′-methyl-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione (3) as grey solid. Yield: 2.15 g, 87%; MS (ESI) m/z 385.5 [M+1]+.

Workup

  1. customAfter completion, solvent was evaporated under reduced pressure
  2. washthe crude was washed with water (50 mL)
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-2d8b284d7e1c40929504874167333a72
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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