Sulfoxonium, trimethyl-, iodide (1:1) → HCID 118598869, compound

HRID 1050369Notes

Reaction equation

HRID 1050369 reaction equation
C[C:2]([CH3:5])([O-:4])[CH3:3].[K+].[I-].[CH3:8][S+](C)(C)=O.[CH3:13][O:14][C:15]1[CH:56]=[CH:55][C:18]([CH2:19][N:20]2[C:48](=[O:49])[C:23]3=C(C4CO4)[CH:25]=[C:26]([N:29]([CH2:36][C:37]4[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=4)[C:30]4[CH:35]=[CH:34][N:33]=[CH:32][N:31]=4)[C:27](=[O:28])[N:22]3[C:21]32[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]3)=[CH:17][CH:16]=1>C(O)(C)(C)C.CS(C)=O>[CH3:13][O:14][C:15]1[CH:56]=[CH:55][C:18]([CH2:19][N:20]2[C:48](=[O:49])[C:23]3=[C:3]([CH:2]4[CH2:5][CH2:8][O:4]4)[CH:25]=[C:26]([N:29]([CH2:36][C:37]4[CH:38]=[CH:39][C:40]([O:43][CH3:44])=[CH:41][CH:42]=4)[C:30]4[CH:35]=[CH:34][N:33]=[CH:32][N:31]=4)[C:27](=[O:28])[N:22]3[C:21]32[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]3)=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 23665647Potassium tert-butoxideHCID 118598658HCID 118598658, compound

Product 1

HCID 118598869HCID 118598869, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
50 °C

Procedure

Potassium tert-butoxide (0.23 g, 2.02 mmol) is added to a solution of trimethylsulfoxonium iodide (0.44 g, 2.02 mmol) in tert-butanol (10 mL) at room temperature. After 15 min, a solution of 2′-(4-methoxybenzyl)-6′-(4-methoxybenzyl)(pyrimidin-4-yl)amino)-8′-(oxiran-2-yl)-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione (5, 1 g, 1.68 mmol) in dimethylsulfoxide (5 mL) is added dropwise. The reaction is stirred at 50° C. overnight. The resulting mixture is quenched with brine and extracted with ethyl acetate. The combined extracts are dried over magnesium sulfate. After filtration and concentration, the residue is purified by flash column to afford 2′-(4-methoxybenzyl)-6′-((4-methoxybenzyl)(pyrimidin-4-yl)amino)-8′-(oxetan-2-yl)-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione (6).

Workup

  1. customThe resulting mixture is quenched with brine
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined extracts are dried over magnesium sulfate
  4. filtrationAfter filtration and concentration
  5. customthe residue is purified by flash column

Sources & evidence

ORD record
ord-8e51b1a656174834990a18a6a65a3a89
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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