Acetic Acid → HCID 178433911, compound

HRID 2243218Notes

Reaction equation

HRID 2243218 reaction equation
Cl.Cl.[NH2:3]N.C[N:6](/[CH:8]=[N:9]/[C:10]([C:12]1([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([S:24][C:25]3[CH:30]=[CH:29][C:28]([N:31]4[C:35](=[O:36])[NH:34][C:33]([CH3:37])=[N:32]4)=[CH:27][CH:26]=3)[CH:19]=2)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=O)C.C(O)(=O)C.CO>[OH-].[Na+].O1CCOCC1.C(OCC)(=O)C>[CH3:37][C:33]1[NH:34][C:35](=[O:36])[N:31]([C:28]2[CH:29]=[CH:30][C:25]([S:24][C:20]3[CH:21]=[CH:22][CH:23]=[C:18]([C:12]4([C:10]5[NH:9][CH:8]=[N:6][N:3]=5)[CH2:13][CH2:14][O:15][CH2:16][CH2:17]4)[CH:19]=3)=[CH:26][CH:27]=2)[N:32]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 17548Hydrazine, dihydrochlorideHCID 178433912HCID 178433912, compound

Product 1

HCID 178433911HCID 178433911, compound

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

Hydrazine dihydrochloride (1.13 g, 10.75 mmol) in sodium hydroxide solution (5N, 3 mL) was added to a solution of N-[(1E)-(dimethylamino)methylene]-4-(3-{[4-(3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)phenyl]thio}phenyl)tetrahydro-2H-pyran-4-carboxamide (3.0 g, 2.15 mmol) (example 11) in 1,4-dioxane. Glacial acetic acid (30 mL, 70%) was added and the reaction mixture was stirred at room temperature for about 30 minutes and then at 90° C. for about 5 hours. The solvent was evaporated under vacuum and a saturated mixture was extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulphate, filtered and the solvent evaporated under vacuum to afford a thick oily residue, which upon column chromatography over silica gel using methanol and ethyl acetate (1:19) afforded the title compound as white crystalline solid. Yield: 1.10 g

Workup

  1. waitat 90° C. for about 5 hours
  2. customThe solvent was evaporated under vacuum
  3. extractiona saturated mixture was extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customthe solvent evaporated under vacuum
  8. customto afford a thick oily residue, which upon column chromatography over silica gel

Sources & evidence

ORD record
ord-6f85b6d2521c48aab7228c7a9ceac6e8
Source dataset
uspto-grants-2010_03
Patent number
US07674811B2

Reaction notes

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