Sodium methanethiolate → HCID 178503677, compound

HRID 81279Notes

Reaction equation

HRID 81279 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]3[N:14]([CH2:20][C@H:21]4[CH2:26][CH2:25][C@H:24]([CH3:27])[CH2:23][CH2:22]4)[C:15]([C:17]([CH3:19])=[CH2:18])=[N:16][C:12]=3[CH:11]=[C:10]([C:28]3[NH:32][C:31](=[O:33])[O:30][N:29]=3)[N:9]=2)[CH:5]=[N:6][CH:7]=1.[CH3:34][S-:35].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]3[N:14]([CH2:20][C@H:21]4[CH2:22][CH2:23][C@H:24]([CH3:27])[CH2:25][CH2:26]4)[C:15]([CH:17]([CH3:19])[CH2:18][S:35][CH3:34])=[N:16][C:12]=3[CH:11]=[C:10]([C:28]3[NH:32][C:31](=[O:33])[O:30][N:29]=3)[N:9]=2)[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 178439857HCID 178439857, compound

Product 1

HCID 178503677HCID 178503677, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

3-[4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-(1-methylethenyl)-3H-imidazo[4,5-c]pyridin-6-yl]-1,2,4-oxadiazol-5(4H)-one (synthesized in a manner similar to Example 9.1; 100 mg, 0.22 mmol) was taken up in MeOH (1.5 mL) at room temperature, and sodium thiomethoxide (376 mg, 5.4 mmol) was added. The reaction was sealed and heated at 65° C. for 2 hours. The reaction was then quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0 to 100% EtOAc/hexanes) to afford 3-{4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[1-methyl-2-(methylsulfanyl)ethyl]-3H-imidazo[4,5-c]pyridin-6-yl}-1,2,4-oxadiazol-5(4H)-one (racemate). 1H NMR (300 MHz, CDCl3) δ 8.69-8.74 (m, 1H), 8.57-8.62 (m, 1H), 8.43 (s, 1H), 7.89-7.94 (m, 1H), 3.71-3.93 (m, 2H), 3.22-3.38 (m, 1H), 3.06-3.19 (m, 1H), 2.88-2.99 (m, 1H), 2.07 (s, 3H), 1.48-1.59 (m, 1H), 1.53 (d, J=6.7 Hz, 3H), 1.22-1.38 (m, 2H), 1.08-1.21 (m, 1H), 0.85-1.07 (m, 3H), 0.78 (d, J=6.4 Hz, 3H), 0.66-0.75 (m, 1H), 0.47-0.66 (m, 2H); MS ES calc'd. for C25H29ClN6O2S [M+H]+ 513. found 513.

Workup

  1. customThe reaction was sealed
  2. customThe reaction was then quenched with saturated ammonium chloride
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (0 to 100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a851d166a2aa4226997dedae65ba8ed3
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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