Benzhydrylamine → N-diphenylmethyl-3-cyanoandrosta-3,5-diene-17beta-carboxamide

HRID 962711노트

반응식

HRID 962711 반응식
[CH:1]([NH2:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]([C:17]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C:19](=[CH:20][CH2:21][C@@H:22]3[C@@H:31]2[CH2:30][CH2:29][C@@:27]2([CH3:28])[C@H:23]3[CH2:24][CH2:25][C@@H:26]2[C:36](O)=[O:37])[CH:18]=1)#[N:16].C(N(CC)CC)C.S(Cl)(C1C=CC(C)=CC=1)(=O)=O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:2]1([CH:1]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:14][C:36]([C@H:26]2[CH2:25][CH2:24][C@H:23]3[C@H:22]4[C@H:31]([CH2:30][CH2:29][C@:27]23[CH3:28])[C@:32]2([CH3:35])[C:19]([CH:18]=[C:17]([C:15]#[N:16])[CH2:34][CH2:33]2)=[CH:20][CH2:21]4)=[O:37])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 7036BenzhydrylamineHCID 73974-Toluenesulfonyl chloride2회HCID 8471TriethylamineHCID 153802543-Cyanoandrosta-3,5-diene-17beta-carboxylic acid

생성물 1

HCID 15380255N-diphenylmethyl-3-cyanoandrosta-3,5-diene-17beta-carboxamide수율 92%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

0.106 ml of benzhydrylamine were added to a solution of 100 mg of 3-cyanoandrosta-3,5-diene-17β-carboxylic acid [prepared as described in Example 1(b)], a catalytic amount of 4-dimethylaminopyridine and 0.131 ml of triethylamine in 4 ml of methylene chloride. 88.0 mg of tosyl chloride were then divided into three portions and added to this reaction mixture at 30 minute intervals at room temperature, whilst stirring. One hour after finishing the addition of the tosyl chloride, the reaction mixture was diluted with methylene chloride, and washed with 1N aqueous hydrochloric acid, with water, with an 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 crystallized from acetone, to give 138 mg (yield 92%) of the title compound.

후처리

  1. additionadded to this reaction mixture at 30 minute intervals at room temperature
  2. customOne hour
  3. washwashed with 1N aqueous hydrochloric acid, with water, with an aqueous solution of sodium hydrogencarbonate
  4. dry with materialIt was then dried over anhydrous magnesium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe resulting residue was crystallized from acetone

출처 및 근거

ORD 기록
ord-168b1004934349e0aed2f32799abb950
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05760025

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