1-Hydroxybenzotriazole → 5-Oxotetrahydrofuran-3-carboxylic acid [1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-yl]amide

HRID 83523ノート

反応式

HRID 83523 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.[O:22]=[C:23]1[O:27][CH2:26][CH:25]([C:28](O)=[O:29])[CH2:24]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.C(=O)([O-])O.[Na+]>CN(C)C=O.O1CCCC1.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]([CH:25]3[CH2:24][C:23](=[O:22])[O:27][CH2:26]3)=[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 110516762-Oxooxolane-4-carboxylic acidHCID 712877391-Phenyl-5-(3-propylphenyl)-1H-pyrazol-3-ylamine

生成物 1

HCID 712877685-Oxotetrahydrofuran-3-carboxylic acid [1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-yl]amide収率 62.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21974620tetrahydrofuran N,N-dimethylformamide溶媒

実験手順

To a solution of 1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-ylamine (109 mg) prepared according to the same procedures as Preparation 8 in N,N-dimethylformamide/tetrahydrofuran (1/1, 2 ml) were sequentially added 5-oxotetrahydrofuran-3-carboxylic acid (82 mg) prepared in Preparation 9, HOBt.H2O (96 mg) and WSC.HCl (121 mg), and the mixture was stirred at room temperature overnight. To this reaction solution was added a saturated aqueous solution of sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The separated organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=10/1) to give the titled compound (96 mg).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationThe separated organic layer was concentrated under reduced pressure
  3. 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-dbfc8e69898741b3a4ae3b4587b7a509
出典データセット
uspto-grants-2014_09
特許番号
US08846746B2

反応ノート

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