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Water → 2-Amino-4-(2-bromo-1,3-thiazol-4-yl)-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulfanyl)pyridine-3,5-dicarbonitrile

HRID 1969476
ノート
印刷プレビュー

反応式

HRID 1969476 の反応式
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[N:11]=[C:12]([Br:15])[S:13][CH:14]=2)[C:5]([C:16]#[N:17])=[C:4]([SH:18])[N:3]=1.Cl[CH2:20][C:21]1[N:22]=[C:23]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[S:24][CH:25]=1.C(=O)(O)[O-].[Na+].O>CN(C=O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[N:11]=[C:12]([Br:15])[S:13][CH:14]=2)[C:5]([C:16]#[N:17])=[C:4]([S:18][CH2:20][C:21]2[N:22]=[C:23]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[S:24][CH:25]=2)[N:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 6102974-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazoleHCID 178510491HCID 178510491、化合物

生成物 1

HCID 668979732-Amino-4-(2-bromo-1,3-thiazol-4-yl)-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulfanyl)pyridine-3,5-dicarbonitrile収率 17%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

4.78 g (purity 77%, 10.882 mmol) of 2-amino-4-(2-bromo-1,3-thiazol-4-yl)-6-sulfanylpyridine-3,5-dicarbonitrile were initially charged in 30 ml of DMF, 2.923 g (11.971 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole and 2.742 g (32.647 mmol) of sodium bicarbonate were added and the mixture was stirred at room temperature overnight. The reaction mixture was added to water, and the precipitated solid was filtered off with suction, washed with water and dried under high vacuum. The contaminated product was applied to silica gel and purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 2:1). The product-containing fractions were concentrated, the residue was triturated with dichloromethane and the solid was filtered off, washed with dichloromethane and dried under high vacuum. This gave 1.1 g of the target compound in a purity of 91% (yield: 17% of theory).

後処理

  1. filtrationthe precipitated solid was filtered off with suction
  2. washwashed with water
  3. customdried under high vacuum
  4. custompurified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 2:1)
  5. concentrationThe product-containing fractions were concentrated
  6. customthe residue was triturated with dichloromethane
  7. filtrationthe solid was filtered off
  8. washwashed with dichloromethane
  9. customdried under high vacuum

出典と根拠

ORDレコード
ord-c9cba4102400471b958ace2d8c8f215c
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08426602B2

反応ノート

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