1-Pyrrolidinepropanamine → 1-(4-{[3-(4-Tert-butylphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]methyl}pyridin-2-yl)-3-(3-pyrrolidin-1-ylpropyl)urea

HRID 546584

反応式

HRID 546584 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[N:13]([CH2:19][C:20]3[CH:25]=[CH:24][N:23]4[O:26][C:27](=S)[N:28]=[C:22]4[CH:21]=3)[C:12]2=[O:30])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N:31]1([CH2:36][CH2:37][CH2:38][NH2:39])[CH2:35][CH2:34][CH2:33][CH2:32]1>CS(C)=O.O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[N:13]([CH2:19][C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH:28][C:27]([NH:39][CH2:38][CH2:37][CH2:36][N:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)=[O:26])[CH:21]=3)[C:12]2=[O:30])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 2

HCID 316701-PyrrolidinepropanamineHCID 576259753-(4-tert-butylphenyl)-5,5-dimethyl-1-[(2-thioxo-2H-[1,2,4]oxadiazolo[2,3-a]pyridin-7-yl)methyl]imidazolidine-2,4-dione

生成物 1

HCID 576260001-(4-{[3-(4-Tert-butylphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]methyl}pyridin-2-yl)-3-(3-pyrrolidin-1-ylpropyl)urea収率 15.1%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

To a solution of 100 mg of 3-(4-tert-butylphenyl)-5,5-dimethyl-1-[(2-thioxo-2H-[1,2,4]oxadiazolo[2,3-a]pyridin-7-yl)methyl]imidazolidine-2,4-dione obtained in stage b) below in 2 mL of dimethyl sulphoxide are added 120 mg of 3-pyrrolidin-1-ylpropan-1-amine. The solution is stirred at a temperature of 100° C. for 1 hour 40 minutes. After cooling to a temperature in the region of 20° C., the reaction medium is diluted with water, the suspension is filtered and the precipitate is purified by chromatography on a column of silica, eluting with a dichloromethane/methanol/28% aqueous ammonia mixture (gradient from 100/0 to 75/20/5 by volume). 18.5 mg of 1-(4-{[3-(4-tert-butylphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]methyl}pyridin-2-yl)-3-(3-pyrrolidin-1-ylpropyl)urea are obtained in the form of a pale yellow powder, the characteristics of which are as follows:

後処理

  1. temperatureAfter cooling to a temperature in the region of 20° C.
  2. filtrationthe suspension is filtered
  3. customthe precipitate is purified by chromatography on a column of silica
  4. washeluting with a dichloromethane/methanol/28% aqueous ammonia mixture (gradient from 100/0 to 75/20/5 by volume)

出典と根拠

ORDレコード
ord-dc8ebb03c0744150885449c27609e79f
出典データセット
uspto-grants-2011_05
特許番号
US07935819B2

関連ノート

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