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

HRID 1404710Notes

Reaction equation

HRID 1404710 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-c3dbcae2fb644b3d9f51795f44c77d04
Source dataset
uspto-grants-2014_12
Patent number
US08912338B2

Reaction notes

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