HCID 66613929, compound → HCID 66634585, compound

HRID 1404715Notes

Reaction equation

HRID 1404715 reaction equation
[C:1]([C:3]([CH3:23])([CH2:20][S:21][CH3:22])[C:4]([N:6]([C:8]1[S:9][C:10]([C:13]2[CH:14]=[N:15][CH:16]=[C:17]([F:19])[CH:18]=2)=[N:11][N:12]=1)[CH3:7])=[O:5])#[N:2].[H][H]>C(O)(=O)C.[Pt]=O>[NH2:2][CH2:1][C:3]([CH3:23])([CH2:20][S:21][CH3:22])[C:4]([N:6]([C:8]1[S:9][C:10]([C:13]2[CH:14]=[N:15][CH:16]=[C:17]([F:19])[CH:18]=2)=[N:11][N:12]=1)[CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 66613929HCID 66613929, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66634585HCID 66634585, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A suspension of 2-cyano-N-[5-(5-fluoro-3-pyridyl)-1,3,4-thiadiazol-2-yl]-N,2-dimethyl-3-methylsulfanyl-propanamide (157 mg, 0.4 mmol) and platinum oxide (131 mg, 0.6 mmol) in glacial acetic acid (8 mL) was reduced under 45 psi of hydrogen at room temperature for 16 hours, filtered through Celite and concentrated under reduced pressure. The residue was treated with saturated aqueous sodium bicarbonate (30 mL) and extracted with ethyl acetate (3×50 mL). Organic extracts were concentrated under reduced pressure and purified by reversed phase silica chromatography eluting with an aqueous acetonitrile mobile phase. Yield 33 mg (21%): mp 154-157° C.; IR (KBr thin film) 1656, 1383 cm−1; 1H NMR (400 MHz, CDCl3) δ 11.17 (br, 1H), 9.02 (t, J=1.6 Hz, 1H), 8.43 (d, J=2.8 Hz, 1H), 8.11 (ddd, J=9.8, 2.8, 1.8 Hz, 1H), 3.87 (d, J=2.9 Hz 1H), 3.48 (s, 3H), 3.47 (d, J=2.9 Hz, 1H), 2.99 (d, J=12.7 Hz, 1H), 2.78 (d, J=13.6 Hz, 1H), 2.20 (s, 3H), 1.41 (s, 3H); ESIMS (m/z) 356 [M+H]+.

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was treated with saturated aqueous sodium bicarbonate (30 mL)
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. concentrationOrganic extracts were concentrated under reduced pressure
  6. custompurified by reversed phase silica chromatography
  7. washeluting with an aqueous acetonitrile mobile phase

Sources & evidence

ORD record
ord-92a8cffe43d846c89ca994f056c00039
Source dataset
uspto-grants-2014_12
Patent number
US08912338B2

Reaction notes

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