HCID 25121515, compound → HCID 25121516, compound

HRID 2400586Notes

Reaction equation

HRID 2400586 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:14]=[C:15]([C:18]4[CH:22]=[C:21]([CH3:23])[N:20]([CH2:24][C:25]5[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=5)[N:19]=4)[O:16][CH:17]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[H][H]>C(O)C.[Pd]>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:13]3[N:14]=[C:15]([C:18]4[CH:22]=[C:21]([CH3:23])[N:20]([CH2:24][C:25]5[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=5)[N:19]=4)[O:16][CH:17]=3)=[CH:11][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 25121515HCID 25121515, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 25121516HCID 25121516, compoundYield 43.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-(4-cyclohex-1-en-1-ylphenyl)-2-[5-methyl-1-(4-methylbenzyl)-1H-pyrazol-3-yl]-1,3-oxazole (Example 80, 30 mg, 0.073 mmol) in ethanol (1.5 ml) was hydrogenated in a continuous-flow reactor (H-cube, Thales Nano, Hungary) at an hydrogen pressure of 1 bar at rt with a flow rate of 1 ml/min using palladium (10% on charcoal) as a stationary phase. After evaporation of the solvent, the crude material was purified by preparative HPLC to afford the title compound as a white solid (13 mg, 43%): 1H NMR (400 MHz, DMSO-d6) 8.57 (s, 1H), 7.72 (d, 2H), 7.29 (d, 2H), 7.17 (d, 2H), 7.07 (d, 2H), 6.67 (s, 1H), 5.36 (s, 2H), 3.51-3.40 (m, 1H), 2.29 (s, 3H), 2.28 (s, 3H), 1.82-1.69 (m, 4H), 1.48-1.22 (m, 6H); ES-MS m/z 412, HPLC RT (Method D) 3.52 min.

Workup

  1. customat rt
  2. customAfter evaporation of the solvent
  3. customthe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-aafb1945f3544effa1407ee35e94c25c
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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