Triethylamine → N-[5-(5-{[[2-(Diethylamino)ethyl](methyl)amino]sulfonyl}-2-thienyl)-4-methyl-1,3-thiazol-2-YL]acetamide

HRID 1948410Notes

Reaction equation

[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[S:15][C:14]([S:16](Cl)(=[O:18])=[O:17])=[CH:13][CH:12]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.[CH2:27]([N:29]([CH2:34][CH3:35])[CH2:30][CH2:31][NH:32][CH3:33])[CH3:28]>C(Cl)Cl>[CH2:27]([N:29]([CH2:34][CH3:35])[CH2:30][CH2:31][N:32]([CH3:33])[S:16]([C:14]1[S:15][C:11]([C:7]2[S:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:9][C:8]=2[CH3:10])=[CH:12][CH:13]=1)(=[O:18])=[O:17])[CH3:28]

Participants

Conditions

Temperature: 0 °C

Procedure

5-[2-(acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride, prepared as in Step II of Example 1 (500 mg; 1.48 mmol; 1.00 eq) is dissolved in DCM (30 ml). The solution is degassed with N2 and cooled down to 0° C. Triethylamine (1.0 ml; 7.42 mmol; 5.00 eq) followed by N,N-diethyl-N′-methylethylenediamine (1.2 ml; 7.42 mmol; 5.00 eq) are added. After 1 hour at 0° C., the reaction is complete. The reaction mixture is washed with NaHCO3 sat. (twice) and water (twice). The organic phase is dried over MgSO4, filtered and concentrated under vacuum, affording Compound (20) as a beige solid (570 mg; 89%).

Workup

customThe solution is degassed with N2
additionare added
washThe reaction mixture is washed with NaHCO3 sat. (twice) and water (twice)
dry with materialThe organic phase is dried over MgSO4
filtrationfiltered
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-38f0b99a712e445d89c41e3517bdaad7
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399497B2

Reaction notes

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