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

HRID 2171487Notes

Reaction equation

HRID 2171487 reaction equation
[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>[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

2.2 g (7.22 mmol) of 4-amino-2-(methylsulphonyl)-1,3-thiazole-5-carbonitrile (Example 18A) are dissolved in 24 ml of DMSO, and 1.74 g (10.84 mmol) of N-Boc-ethylenediamine and 933 mg (7.22 mmol) of DIPEA are added. The mixture is stirred at 120° C. for 16 h and, after the reaction is complete, water and ethyl acetate are added. The aqueous phase is extracted three times with ethyl acetate. The combined organic phases are dried over magnesium sulphate and purified by silica gel chromatography. 633 mg (31% of theory) of the product are obtained.

Workup

  1. extractionThe aqueous phase is extracted three times with ethyl acetate
  2. dry with materialThe combined organic phases are dried over magnesium sulphate
  3. custompurified by silica gel chromatography
  4. custom633 mg (31% of theory) of the product are obtained

Sources & evidence

ORD record
ord-2acdcba5c4c84105a6d95fe8728af662
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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