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

HRID 2088652Notes

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>[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]

Participants

Conditions

Temperature: 120 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-23f8430107e7405d82a737e0ecae8022
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436003B2

Reaction notes

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