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

HRID 1948412Notes

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.[CH3:27][N:28]([CH3:34])[CH2:29][CH2:30][NH:31][CH2:32][CH3:33]>C(Cl)Cl>[CH3:27][N:28]([CH3:34])[CH2:29][CH2:30][N:31]([CH2:32][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]

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) 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-dimethyl-N′-ethylethylenediamine (1.2 ml; 7.42 mmol; 5.00 eq) are added. After 30 minutes 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 (22) as a beige solid (544 mg; 88%).

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-078b0eb6ec7d4f6fab61cad75fcb1ea4
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399497B2

Reaction notes

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