Nitrogen → (17beta)-7-methyl-3-oxo-N-[2-(trifluoromethyl)phenyl]androst-5-ene-17-carboxamide

HRID 749053Notes

Reaction equation

HRID 749053 reaction equation
C[Mg]Br.N#N.[O:6]=[C:7]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C:9]([CH:10]=[CH:11][C@@H:12]3[C@@H:21]2[CH2:20][CH2:19][C@@:17]2([CH3:18])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C:26]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]([F:38])([F:37])[F:36])=[O:27])=[CH:8]1.[CH2:39]1COCC1>CCOCC.Cl[Cu]>[CH3:39][CH:11]1[CH:10]=[C:9]2[C@:22]([CH3:25])([CH2:23][CH2:24][C:7](=[O:6])[CH2:8]2)[C@@H:21]2[C@@H:12]1[C@H:13]1[C@@:17]([CH2:19][CH2:20]2)([CH3:18])[C@@H:16]([C:26]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]([F:36])([F:37])[F:38])=[O:27])[CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 947NitrogenHCID 8028TetrahydrofuranHCID 68976085(17beta)-3-oxo-N-[2-(trifluoromethyl)phenyl]androsta-4,6-diene-17-carboxamideHCID 178418573HCID 178418573, compound

Product 1

HCID 69266012(17beta)-7-methyl-3-oxo-N-[2-(trifluoromethyl)phenyl]androst-5-ene-17-carboxamide

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3.0 M methylmagnesium bromide (2.35 mmol) in ether under a stream of N2 was added 6.0 mL degassed THF. The solution was cooled to 0° C., then CuCl (0.03 g, 0.300 mmol) was added. The mixture was stirred for 5 min. A solution of the compound from Step A (5-2) (0.25 g, 0.55 mmol) in 6.0 mL degassed THF was added. The reaction was warmed to room temperature overnight. It was quenched by slow addition of 2.0 mL degassed water, then diluted with 10% KHSO4 solution and EtOAc. The organic phase was washed with 10% KHSO4 solution, saturated NaHCO3 solution, and brine. After removal of the solvent, the residue was purified by preparative HPLC (C18; 70% MeOH with 5 to 30% MeCN-water) to provide 5-5.

Workup

  1. customdegassed THF
  2. additionwas added
  3. temperatureThe reaction was warmed to room temperature overnight
  4. customIt was quenched by slow addition of 2.0 mL
  5. customdegassed water
  6. additiondiluted with 10% KHSO4 solution and EtOAc
  7. washThe organic phase was washed with 10% KHSO4 solution, saturated NaHCO3 solution, and brine
  8. customAfter removal of the solvent
  9. customthe residue was purified by preparative HPLC (C18; 70% MeOH with 5 to 30% MeCN-water)
  10. customto provide 5-5

Sources & evidence

ORD record
ord-fbff93e03b97414db87770a6e489c72a
Source dataset
uspto-grants-2008_07
Patent number
US07402577B2

Reaction notes

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