Phosphorus oxychloride → N-[1-(3,5-Dimethoxyphenyl)-1-methylethyl]-3-cyanoandrosta-3,5-diene-17beta-carboxamide

HRID 862319

반응식

HRID 862319 반응식
P(Cl)(Cl)([Cl:3])=O.[CH3:6][N+:7]([CH3:10])=[CH:8][Cl:9].[Cl-].[C:12]([C:14]1[CH2:31][CH2:30][C@@:29]2([CH3:32])[C:16](=[CH:17][CH2:18][C@@H:19]3[C@@H:28]2[CH2:27][CH2:26][C@@:24]2([CH3:25])[C@H:20]3[CH2:21][CH2:22][C@@H:23]2[C:33](O)=[O:34])[CH:15]=1)#[N:13].[CH3:36][O:37][C:38]1[CH:39]=[C:40]([C:46]([NH2:49])([CH3:48])[CH3:47])[CH:41]=[C:42]([O:44][CH3:45])[CH:43]=1>C(Cl)Cl.C(OCC)(=O)C.CC(C)=O.C(N(CC)CC)C.CN(C)C=O>[CH3:6][N+:7]([CH3:10])=[CH:8][Cl:9].[Cl-:3].[CH3:45][O:44][C:42]1[CH:41]=[C:40]([C:46]([NH:49][C:33]([C@H:23]2[CH2:22][CH2:21][C@H:20]3[C@H:19]4[C@H:28]([CH2:27][CH2:26][C@:24]23[CH3:25])[C@:29]2([CH3:32])[C:16]([CH:15]=[C:14]([C:12]#[N:13])[CH2:31][CH2:30]2)=[CH:17][CH2:18]4)=[O:34])([CH3:47])[CH3:48])[CH:39]=[C:38]([O:37][CH3:36])[CH:43]=1

참가 물질

11

반응물 4

HCID 24813Phosphorus oxychlorideHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 153802543-Cyanoandrosta-3,5-diene-17beta-carboxylic acidHCID 157541382-(3,5-Dimethoxyphenyl)propan-2-amine

생성물 2

HCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 57001892N-[1-(3,5-Dimethoxyphenyl)-1-methylethyl]-3-cyanoandrosta-3,5-diene-17beta-carboxamide수율 50%

시약·촉매·용매 5

HCID 180Acetone용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매4회HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

Vilsmeier reagent was prepared from 1.7 ml of dimethylformamide, 1.8 ml of phosphorus oxychloride, and 5 ml of methylene chloride. 0.23 ml of this Vilsmeier reagent was then added to a solution of 100 mg of 3-cyanoandrosta-3,5-diene-17β-carboxylic acid [prepared as described in Example 1(b)] in 2 ml of methylene chloride. The reaction mixture was then stirred at room temperature for 40 minutes, after which a solution of 1-(3,5-dimethoxyphenyl)-1-methylethylamine [prepared as described in Preparation 10(d)] and 70 μl of triethylamine in 2 ml of methylene chloride were added. The reaction mixture was then diluted with ethyl acetate, washed with dilute aqueous hydrochloric acid, with an aqueous solution of sodium chloride, with a 5% w/v aqueous solution of sodium hydrogencarbonate, and with a saturated aqueous solution of sodium chloride, in that order. It was then dried over anhydrous magnesium sulfate, and concentrated by evaporation under reduced pressure. The resulting residue was subjected to silica gel column chromatography and using a gradient elution method, with solutions of from 1 to 4% by volume of acetone in methylene chloride as the eluent, to give 76 mg (yield 50%) of the title compound.

후처리

  1. washwashed with dilute aqueous hydrochloric acid, with an aqueous solution of sodium chloride, with a 5% w/v aqueous solution of sodium hydrogencarbonate
  2. dry with materialIt was then dried over anhydrous magnesium sulfate
  3. concentrationconcentrated by evaporation under reduced pressure
  4. washa gradient elution method

출처 및 근거

ORD 기록
ord-3c8507c9300646b1a0ccec927ca681ee
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05717088

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