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

HRID 444814ノート

反応式

HRID 444814 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].C(N(CC)C(C)C)(C)C>CS(C)=O.C(OCC)(=O)C.O>[NH2:1][C:2]1[N:3]=[C:4]([NH:23][CH2:22][CH2:21][NH:20][C:13](=[O:14])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])[S:5][C:6]=1[C:7]#[N:8]

参加物

7

反応物 3

HCID 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 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

3.25 g (16 mmol) of 4-amino-2-(methylsulfonyl)-1,3-thiazole-5-carbonitrile (Example 6A) were dissolved in 50 ml of DMSO, and 3.8 g (24 mmol) of N-Boc-ethylenediamine and 2.8 ml (16 mmol) of N,N-diisopropylethylamine were added. The mixture was stirred at 120° C. for 12 h. The reaction mixture was taken up in a mixture of ethyl acetate and water. The organic phase was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated on a rotary evaporator. The crude product was triturated with acetonitrile and the precipitated crystals were filtered off with suction. This gave 2.5 g (55% of theory) of the product as a solid.

後処理

  1. washThe organic phase was washed with saturated aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated on a rotary evaporator
  4. customThe crude product was triturated with acetonitrile
  5. filtrationthe precipitated crystals were filtered off with suction

出典と根拠

ORDレコード
ord-b57f40c64f934835bf68eda16cb8c0d0
出典データセット
uspto-grants-2013_07
特許番号
US08476267B2

反応ノート

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