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

HRID 57666Notes

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].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]

Participants

Conditions

Temperature: 120 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-54b3b810aa7644a5ac543aae362f507d
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434731B2

Reaction notes

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