Sodium Acetate → (4E)-4-methoxyimino-N-methyl-N-(5-pyridin-3-yl-1,3,4-thiadiazol-2-yl)pentanamide

HRID 1911971Notes

Reaction equation

HRID 1911971 reaction equation
Cl.[CH3:2][O:3][NH2:4].[CH3:5][N:6]([C:14]1[S:15][C:16]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[N:17][N:18]=1)[C:7](=[O:13])[CH2:8][CH2:9][C:10](=O)[CH3:11].C([O-])(=O)C.[Na+]>C(O)C>[CH3:5][N:6]([C:14]1[S:15][C:16]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[N:17][N:18]=1)[C:7](=[O:13])[CH2:8][CH2:9]/[C:10](=[N:4]/[O:3][CH3:2])/[CH3:11]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 66613626N-methyl-4-oxo-N-[5-(3-pyridyl)-1,3,4-thiadiazol-2-yl]pentanamide

Product 1

HCID 73332623(4E)-4-methoxyimino-N-methyl-N-(5-pyridin-3-yl-1,3,4-thiadiazol-2-yl)pentanamideYield 37.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-[(E)-methoxyimino]-pentanoic acid methyl-(5-pyridin-3-yl-[1,3,4]thiadiazol-2-yl)-amide was prepared as described in J F W Keana et al. in J. Org. Chem., 1985, 50, 2346. A suspension of O-methylhydroxylamine hydrochloride (0.065 g, 0.9 mmol), 4-oxo-pentanoic acid methyl-(5-pyridin-3-yl-[1,3,4]thiadiazol-2-yl)-amide (0.18 g, 0.6 mmol) and sodium acetate (0.076 g, 0.9 mmol) in anhydrous ethanol was refluxed under nitrogen for 14 hours, cooled, concentrated under reduced pressure and chromatographed on silica to afford the title compound as an amorphous yellow solid (0.071 g, 36%): mp 114-121° C.; 1H NMR (400 MHz, CDCl3) δ 9.15 (d, J=1.8 Hz, 1H), 8.70 (dd, J=4.8, 1.8 Hz, 1H), 8.29 (dt, J=5.9, 1.8 Hz, 1H), 7.43 (dd, J=7.7, 5.2 Hz, 1H), 3.92 (s, 3H), 3.86, 3.83 and 3.77 (all s, 1H), 2.95 (q, J=7.0 Hz, 2H), 2.71 (q, J=7.4 Hz, 2H), 2.11, 1.98 and 1.89 (all s, 3H); ESIMS m/z 320 ([M+H]+).

Workup

  1. custom4-[(E)-methoxyimino]-pentanoic acid methyl-(5-pyridin-3-yl-[1,3,4]thiadiazol-2-yl)-amide was prepared
  2. temperaturewas refluxed under nitrogen for 14 hours
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure
  5. customchromatographed on silica

Sources & evidence

ORD record
ord-6e6cc97b6ac942f982daaadf04a92ec3
Source dataset
uspto-grants-2013_12
Patent number
US08604211B2

Reaction notes

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