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1,2-二氯乙烷 → N-{3,4-Dioxo-1-phenyl-4-[(2-phenylethyl)amino]butan-2-yl}-2-[3-(4-fluorophenyl)-1H-pyrazol-1-yl]pyridine-3-carboxamide

HRID 1908262
笔记
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反应方程式

HRID 1908262 反应方程式
C(Cl)CCl.ClC(Cl)C(O)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:22]=[CH:21][N:20]([C:23]3[N:52]=[CH:51][CH:50]=[CH:49][C:24]=3[C:25]([NH:27][CH:28]([CH:36]([OH:48])[C:37](=[O:47])[NH:38][CH2:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:26])[N:19]=2)=[CH:14][CH:13]=1.C([O-])(O)=O.[Na+]>CS(C)=O.[Cl-].[Na+].O>[O:48]=[C:36]([C:37](=[O:47])[NH:38][CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH:28]([NH:27][C:25]([C:24]1[C:23]([N:20]2[CH:21]=[CH:22][C:18]([C:15]3[CH:14]=[CH:13][C:12]([F:11])=[CH:17][CH:16]=3)=[N:19]2)=[N:52][CH:51]=[CH:50][CH:49]=1)=[O:26])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1
参与物实验过程后处理来源与证据反应笔记

参与物

7

反应物 4

HCID 111,2-二氯乙烷HCID 6597Dichloroacetic AcidHCID 516892碳酸氢钠HCID 672384272-(3-(4-Fluorophenyl)-1H-pyrazol-1-yl)-N-(3-hydroxy-4-oxo-4-(phenethylamino)-1-phenylbutan-2-yl)nicotinamide

产物 1

HCID 67238275N-{3,4-Dioxo-1-phenyl-4-[(2-phenylethyl)amino]butan-2-yl}-2-[3-(4-fluorophenyl)-1H-pyrazol-1-yl]pyridine-3-carboxamide收率 48.3%

试剂、催化剂与溶剂 2

HCID 679二甲基亚砜溶剂HCID 57417360Sodium chloride; water溶剂

实验过程

EDC (520 mg, 2.71 mmol) and 2,2-dichloroacetic acid (0.14 ml, 1.69 mmol) were added to a solution of 2-(3-(4-fluorophenyl)-1H-pyrazol-1-yl)-N-(3-hydroxy-4-oxo-4-(phenethylamino)-1-phenylbutan-2-yl)nicotinamide (191 mg, 0.339 mmol) in dimethyl sulfoxide (DMSO) (9 ml), and the reaction mixture was stirred for 45 minutes at room temperature. For work up the reaction mixture was mixed with 100 ml of brine and sat. solution of NaHCO3 (1:1(v/v)) for 10 minutes. The resulting solid was filtered off with suction, washed with water and dried to give 161 mg of the crude product, which was re-crystallized from ethyl acetate to give 92 mg of a white amorphous solid; ESI-MS [M+H]+: 562.3.

后处理

  1. filtrationThe resulting solid was filtered off with suction
  2. washwashed with water
  3. customdried
  4. customto give 161 mg of the crude product, which
  5. customwas re-crystallized from ethyl acetate

来源与证据

ORD记录
ord-e6c8683922ab4d65906b8bb9e40a132f
来源数据集
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
专利号
US08598211B2

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