HCID 18441739, compound → HCID 18441748, compound

HRID 458157Notes

Reaction equation

HRID 458157 reaction equation
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9]([C:12]3([C:24]#N)[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]3[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:8][CH2:7]2)[N:5]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:4][NH:3]1.C[Mg]Br>C1COCC1>[CH3:24][C:12]1([N:9]2[CH2:8][CH2:7][C:6]3([N:5]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:4][NH:3][C:2]3=[O:1])[CH2:11][CH2:10]2)[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 18441739HCID 18441739, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 18441748HCID 18441748, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 20 mg (0.048 mmol) 1-(4-oxo-1-phenyl-1,3,8-triaza-spiro[4.5]dec-8-yl)-2-phenyl-cyclohexane-carbonitrile in 1.5 ml dry THF under argon at 0° C. were added 0.03 ml (0.096 mmol) methyl magnesium bromide (3M solution in THF) and the resulting mixture heated to reflux for 3.5 h. The reaction mixture was cooled to ambient temperature, quenched by the addition of water and the product extracted with ethyl acetate. The combined organic extracts were then washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by chromatography on silica gel eluting with hexane/ethyl acetate: 10 mg 8-(1-methyl-2-phenyl-cyclohexyl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one as colorless solid; MS (ISP): 404.6 MH+.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureto reflux for 3.5 h
  3. customquenched by the addition of water
  4. extractionthe product extracted with ethyl acetate
  5. washThe combined organic extracts were then washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by chromatography on silica gel eluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-12b0a7b1b48641aa8eaf428db250f42d
Source dataset
uspto-grants-2007_03
Patent number
US07189850B2

Reaction notes

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