Water → HCID 118599129, compound

HRID 1050392Notes

Reaction equation

HRID 1050392 reaction equation
[OH:1][C:2]1[C:7](=[O:8])[N:6]2[C:9]3([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[NH:10][C:11](=[O:12])[C:5]2=[C:4]([CH3:18])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:25]1([C:28]([NH2:30])=O)[CH2:27]C1.O.C[C:33]([N:35](C)C)=O>>[CH3:18][C:4]1[CH:3]=[C:2]([O:1][C:28]2[CH:25]=[CH:27][N:35]=[CH:33][N:30]=2)[C:7](=[O:8])[N:6]2[C:9]3([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[NH:10][C:11](=[O:12])[C:5]=12

Participants

6

Reactant 5

HCID 962WaterHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 80376CyclopropanecarboxamideHCID 118598829HCID 118598829, compound

Product 1

HCID 118599129HCID 118599129, compound

Conditions

Temperature
130 °C

Procedure

To a solution of 6′-hydroxy-8′-methyl-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione (3, 1 g, 4.03 mmol) in dimethylacetamide (20 mL) is added potassium carbonate (1.67 g, 12.09 mmol) and 4-bromopyrimidine (4, 0.77 g, 4.84 mmol). The reaction is stirred at 130° 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 8′-methyl-6′-(pyrimidin-4-yloxy)-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione (Cpd. No. 209).

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-bf25e911a576401db74429762d3430c7
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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