1-Hydroxybenzotriazole → (R)-3-methyl-2-oxoimidazolidine-4-carboxylic acid[1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-yl]amide

HRID 83520ノート

反応式

HRID 83520 の反応式
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][CH3:20])[CH:13]=3)=[CH:10][C:9]([NH2:21])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:22][N:23]1[C@@H:27]([C:28](O)=[O:29])[CH2:26][NH:25][C:24]1=[O:31].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.C(=O)([O-])O.[Na+]>CN(C)C=O.O>[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][CH3:20])[CH:13]=3)=[CH:10][C:9]([NH:21][C:28]([C@H:27]3[CH2:26][NH:25][C:24](=[O:31])[N:23]3[CH3:22])=[O:29])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

8

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 712877391-Phenyl-5-(3-propylphenyl)-1H-pyrazol-3-ylamineHCID 86680360HCID 86680360、化合物

生成物 1

HCID 89465846(R)-3-methyl-2-oxoimidazolidine-4-carboxylic acid[1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-yl]amide収率 49.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-ylamine (56 mg) prepared according to the same procedures as Preparation 8 in N,N-dimethylformamide (0.6 ml) were sequentially added (R)-3-methyl-2-oxoimidazolidine-4-carboxylic acid (38 mg) prepared in Preparation 9, HOBt.H2O (46 mg) and WSC.HCl (58 mg), and the mixture was stirred at room temperature for 2 hours. To this reaction solution were added a saturated aqueous solution of sodium hydrogen carbonate and water, and the mixture was extracted with ethyl acetate. The separated organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=10/1) to give the titled compound (40 mg).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe separated organic layer was washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=10/1)

出典と根拠

ORDレコード
ord-44c1071b94dc44dcbee7f8412b2b78be
出典データセット
uspto-grants-2014_09
特許番号
US08846746B2

反応ノート

読み込み中…