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

HRID 2389747Notes

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

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

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

Sources & evidence

ORD record: ord-08d9cbe1dce84dc6a9c2bf913844b8ad
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273752B2

Reaction notes

Loading…