HCID 178509416, compound → HCID 178509417, compound

HRID 2091698Notes

Reaction equation

HRID 2091698 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:25]#[N:26])=[C:11]([C:19]2[CH2:20][CH2:21][O:22][CH2:23][CH:24]=2)[S:12][C:13]=1[C:14]1[NH:18][CH:17]=[N:16][N:15]=1>CO.[Pd]>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:25]#[N:26])=[C:11]([CH:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[S:12][C:13]=1[C:14]1[NH:18][CH:17]=[N:16][N:15]=1

Participants

4

Reactant 1

HCID 178509416HCID 178509416, compound

Product 1

HCID 178509417HCID 178509417, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-(2,4-dichlorophenyl)-2-(3,6-dihydro-2H-pyran-4-yl)-5-(4H-1,2,4-triazol-3-yl)thiophene-3-carbonitrile (20 mg, 0.05 mmol) was dissolved in methanol (2 mL) and 10% Pd/C was added (10 mg). The mixture was stirred under an atmosphere of hydrogen for 2 hours. The suspension was filtered through celite, solvent was evaporated and the residue was purified using ISCO chromatography on silica gel, elution 20% ethyl acetate in hexanes to ethyl acetate to afford the title compound (16 mg, 80%). LCMS: (FA) ES+, 405. 1H NMR (400 MHz, d4-methanol) δ: 8.53 (s, 1H), 7.78 (d, 1H), 7.51-7.46 (m, 2H), 4.12-4.08 (m, 1H), 3.99-3.95 (m, 1H), 3.53-3.30 (m, 2H), 3.20-3.15 (m, 1H), 2.00-1.95 (m, 1H), 1.83-1.72 (m, 1H).

Workup

  1. filtrationThe suspension was filtered through celite, solvent
  2. customwas evaporated
  3. customthe residue was purified
  4. washon silica gel, elution 20% ethyl acetate in hexanes to ethyl acetate

Sources & evidence

ORD record
ord-6abf27d254ec4a2db391a46f35e1f02b
Source dataset
uspto-grants-2013_05
Patent number
US08440664B2

Reaction notes

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