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

HRID 749053ノート

反応式

HRID 749053 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 62652Cuprous chloride触媒HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fbff93e03b97414db87770a6e489c72a
出典データセット
uspto-grants-2008_07
特許番号
US07402577B2

反応ノート

読み込み中…