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

HRID 2088652
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HRID 2088652 반응식
[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]
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참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide
용매
HCID 8857Ethyl Acetate용매

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온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-23f8430107e7405d82a737e0ecae8022
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08436003B2

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