HCID 118598560, compound → HCID 118598622, compound

HRID 1050394Notes

Reaction equation

HRID 1050394 reaction equation
Cl[C:2]1[N:7]=[C:6]([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)[CH:5]=[CH:4][N:3]=1>C(O)(=O)C.[Cu].[Zn]>[CH3:25][C:11]1[CH:10]=[C:9]([S:8][C:6]2[CH:5]=[CH:4][N:3]=[CH:2][N:7]=2)[C:14](=[O:15])[N:13]2[C:16]3([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]3)[NH:17][C:18](=[O:19])[C:12]=12

Participants

4

Reactant 1

HCID 118598560HCID 118598560, compound

Product 1

HCID 118598622HCID 118598622, compound

Reagents, catalysts & solvents 2

HCID 10290809Zinc copper coupleCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 6′-((2-chloropyrimidin-4-yl)thio)-8′-methyl-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione (6, 0.3 g, 0.80 mmol) in acetic acid (4 mL) is added zinc copper couple (0.5 g). The reaction is stirred at reflux for 4 h. The resulting mixture is cooled to room temperature, filtered and concentrated. The crude is purified via column chromatography to afford 8′-methyl-6′-(pyrimidin-4-ylthio)-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione (Cpd. No. 210).

Workup

  1. temperatureat reflux for 4 h
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe crude is purified via column chromatography

Sources & evidence

ORD record
ord-bffc601d50c640258ffe4b20f3924068
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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