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

HRID 83523노트

반응식

HRID 83523 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 21974620tetrahydrofuran N,N-dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-dbfc8e69898741b3a4ae3b4587b7a509
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846746B2

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