HCID 131734596, compound → HCID 125487788, compound

HRID 595856Notes

Reaction equation

HRID 595856 reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][CH2:12][C:11]([C:15]2[N:16]=[CH:17][C:18]([NH2:21])=[N:19][CH:20]=2)=[CH:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CO.[Pd]>[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][CH2:12][C@@H:11]([C:15]2[N:16]=[CH:17][C:18]([NH2:21])=[N:19][CH:20]=2)[CH2:10]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 131734596HCID 131734596, compound

Product 1

HCID 125487788HCID 125487788, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst3×HCID 887MethanolSolvent

Procedure

A mixture of 5-(3-((tert-butyldimethylsilyl)oxy)cyclohex-1-en-1-yl)pyrazin-2-amine (238 mg, 0.779 mmol) and Pd/C (10%) (50 mg, 0.779 mmol) in MeOH (7.79 mL) was stirred under H2 atmosphere for 3 h. LCMS indicated about 60% conversion. More Pd/C (20 mg) was added, and stirred about another 4 h. LCMS indicated still little amount of starting material left. More Pd/C (20 mg) was added and stirred overnight. Catalyst was filtered out and solvent was evaporated. The residue was purified with flash chromatography eluting with 0-100% of EtOAc/heptane to provide 110 mg of desired cis racemate compound. LCMS (m/z): 308.4 (MH+), 1.01 min.

Workup

  1. stirringstirred about another 4 h
  2. waitleft
  3. stirringstirred overnight
  4. filtrationCatalyst was filtered out
  5. customsolvent was evaporated
  6. customThe residue was purified with flash chromatography
  7. washeluting with 0-100% of EtOAc/heptane
  8. customto provide 110 mg
  9. custom308.4 (MH+), 1.01 min.

Sources & evidence

ORD record
ord-3d866d3dcdda48b98b2937949e05c445
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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