Water → HCID 67352088, compound

HRID 1672790Notes

Reaction equation

HRID 1672790 reaction equation
[SH:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[C:9]([N:13]3[CH2:22][C@H:21]4[N:17]([CH2:18][CH2:19][CH2:20]4)[C:16]4[N:23]=[C:24]([S:27][CH3:28])[N:25]=[CH:26][C:15]=4[C:14]3=[O:29])[CH:10]=[CH:11][CH:12]=2)=[N:4][N:3]=1.[C:30](=O)([O-])[O-].[K+].[K+].CI.O>CN(C=O)C>[CH3:28][S:27][C:24]1[N:25]=[CH:26][C:15]2[C:14](=[O:29])[N:13]([C:9]3[CH:10]=[CH:11][CH:12]=[C:7]([C:5]4[O:6][C:2]([S:1][CH3:30])=[N:3][N:4]=4)[CH:8]=3)[CH2:22][C@H:21]3[N:17]([CH2:18][CH2:19][CH2:20]3)[C:16]=2[N:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178503399HCID 178503399, compound

Product 1

HCID 67352088HCID 67352088, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-5-[3-(5-Mercapto-1,3,4-oxadiazol-2-yl)phenyl]-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (37 mg, 0.09 mmol) obtained in Step 1 was dissolved in DMF (1.0 mL), and the mixture was stirred at room temperature for 1 hour after adding potassium carbonate (36 mg, 0.26 mmol) and methyl iodide (0.012 mL, 0.19 mmol). Thereafter, water was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was then purified by silica gel column chromatography to give (S)-9-methylthio-5-[3-(5-methylthio-1,3,4-oxadiazol-2-yl)phenyl]-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (23 mg, 59%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3a5be3ae4e9041d9b4714b9000c8b076
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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