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

HRID 749053노트

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HRID 749053 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 62652Cuprous chloride촉매HCID 3283Diethyl Ether용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fbff93e03b97414db87770a6e489c72a
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402577B2

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