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三乙胺 → N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide

HRID 589302
笔记
打印预览

反应方程式

HRID 589302 反应方程式
[F:1][CH:2]([F:13])[C:3]1[C:7]([C:8](Cl)=[O:9])=[C:6]([F:11])[N:5]([CH3:12])[N:4]=1.[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[CH:22]([O:26][CH3:27])[CH:23]([NH2:25])[CH3:24].C(N(CC)CC)C.C(OCC)(=O)C>ClCCl>[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[CH:22]([O:26][CH3:27])[CH:23]([NH:25][C:8]([C:7]1[C:3]([CH:2]([F:13])[F:1])=[N:4][N:5]([CH3:12])[C:6]=1[F:11])=[O:9])[CH3:24]
参与物实验过程后处理来源与证据反应笔记

参与物

6

反应物 4

HCID 8471三乙胺HCID 8857乙酸乙酯HCID 529205085-fluoro-1-methyl-3-difluoromethyl-1H-pyrazole-4-carbonyl chlorideHCID 594032951-(2,4-Dichlorophenyl)-1-methoxypropan-2-amine

产物 1

HCID 67963548N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide收率 97.5%

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

实验过程

At ambient temperature, 233 mg (1.1 mmol) of 3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carbonyl chloride and 234 mg (1 mmol) of 1-(2,4-dichlorophenyl)-1-methoxypropan-2-amine are dissolved in 10 ml of dichloromethane. 121 mg (1.2 mmol) of triethylamine are added and the reaction mixture is stirred for 4 hrs at ambient temperature. The mixture is diluted by 50 ml of ethyl acetate and successively washed by a 1 N solution of HCl (twice), a saturated solution of potassium carbonate (twice) and brine and dried over magnesium sulfate. The solvents are removed and the crude amide is purified by column chromatography on silica gel (gradient heptane/ethyl acetate) to yields 400 mg (97% yield) of N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide as a pale yellow solid (M+H=410).

后处理

  1. washsuccessively washed by a 1 N solution of HCl (twice), a saturated solution of potassium carbonate (twice) and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvents are removed
  4. customthe crude amide is purified by column chromatography on silica gel (gradient heptane/ethyl acetate)

来源与证据

ORD记录
ord-70adf4c7930c4a1f822d953fccfe7f3f
来源数据集
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
专利号
US09232799B2

反应笔记

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本页导航参与物实验过程后处理来源与证据反应笔记