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盐酸 → N'-Cyclopropyl-N2-(2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl)-1-benzofuran-2,6-dicarboxamide

HRID 2371069
笔记
打印预览

反应方程式

HRID 2371069 反应方程式
[F:1][C:2]([F:30])([F:29])[CH:3]([NH:14][C:15]([C:17]1[O:18][C:19]2[CH:25]=[C:24]([C:26](O)=[O:27])[CH:23]=[CH:22][C:20]=2[CH:21]=1)=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.[CH:50]1([NH2:53])[CH2:52][CH2:51]1.Cl>CN(C)C=O>[CH:50]1([NH:53][C:26]([C:24]2[CH:23]=[CH:22][C:20]3[CH:21]=[C:17]([C:15]([NH:14][CH:3]([C:4]4[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:12])([F:11])[F:13])[CH:5]=4)[C:2]([F:30])([F:1])[F:29])=[O:16])[O:18][C:19]=3[CH:25]=2)=[O:27])[CH2:52][CH2:51]1
参与物反应条件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 313盐酸HCID 69828环丙胺HCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 582479382-({2,2,2-Trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1-benzofuran-6-carboxylic acid

产物 1

HCID 58247948N'-Cyclopropyl-N2-(2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl)-1-benzofuran-2,6-dicarboxamide

试剂、催化剂与溶剂

1
HCID 6228N,N-二甲基甲酰胺溶剂

反应条件

温度
50 °C

实验过程

A solution of 2-({2,2,2-trifluoro-1-[3-(trifluormethyl)phenyl]ethyl}carbamoyl)-1-benzofuran-6-carboxylic acid (100 mg, 0.21 mmol) in N,N-dimethylformamide (1 ml) was admixed with 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (100 mg, 0.46 mmol) and cyclopropylamine (36 mg, 0.63 mmol), and stirred in a closed vessel at 50° C. overnight. The cooled reaction solution was admixed with hydrochloric acid (1 M) and extracted with ethyl acetate. The organic phase was washed with sat, sodium hydrogencarbonate solution and saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated to dryness under reduced pressure. The residue was chromatographed on a preparative HPLC with water/acetonitrile as the eluent (gradient=43 min from 10%, acetonitrile in water to 100% acetonitrile).

后处理

  1. customThe cooled reaction solution
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed
  4. dry with materialsodium hydrogencarbonate solution and saturated sodium chloride solution, dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe residue was chromatographed on a preparative HPLC with water/acetonitrile as the eluent (gradient=43 min from 10%, acetonitrile in water to 100% acetonitrile)

来源与证据

ORD记录
ord-5a41eb776fbb4d6e866d4bbed58a86c3
来源数据集
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
专利号
US08710242B2

反应笔记

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本页导航参与物反应条件实验过程后处理来源与证据反应笔记