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Water → tert-Butyl{2-[(4-amino-5-cyano-1,3-thiazol-2-yl)amino]ethyl}carbamate

HRID 2088652
ノート
印刷プレビュー

反応式

HRID 2088652 の反応式
[NH2:1][C:2]1[N:3]=[C:4](S(C)(=O)=O)[S:5][C:6]=1[C:7]#[N:8].[C:13]([NH:20][CH2:21][CH2:22][NH2:23])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].CCN(C(C)C)C(C)C.O>CS(C)=O.C(OCC)(=O)C>[C:16]([O:15][C:13](=[O:14])[NH:20][CH2:21][CH2:22][NH:23][C:4]1[S:5][C:6]([C:7]#[N:8])=[C:2]([NH2:1])[N:3]=1)([CH3:19])([CH3:17])[CH3:18]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 187201N-BOC-ethylenediamineHCID 198350775-Thiazolecarbonitrile, 4-amino-2-(methylsulfonyl)-

生成物 1

HCID 57911749tert-Butyl{2-[(4-amino-5-cyano-1,3-thiazol-2-yl)amino]ethyl}carbamate

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

2.2 g (7.22 mmol) of 4-amino-2-(methylsulfonyl)-1,3-thiazole-5-carbonitrile (Example 14A) were dissolved in 24 ml of DMSO, and 1.74 g (10.84 mmol) of N-Boc-ethylenediamine and 933 mg (7.22 mmol) of DIEA were added. The mixture was stirred for 16 h at 120° C., and water and ethyl acetate were added once the reaction had ended. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulfate and purified by silica gel chromatography. This gave 633 mg (31% of theory) of the product.

後処理

  1. extractionThe aqueous phase was extracted three times with ethyl acetate
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-23f8430107e7405d82a737e0ecae8022
出典データセット
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08436003B2

反応ノート

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