Dimethylformamide → 5-(1,1-Dioxo-1lambda6-iso-thiazolidin-2-ylmethyl)-2-(4-isopropylpiperazin-1-yl)benzothiazole
Reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[S:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:22][CH2:23][CH2:24][S:25]([OH:28])(=O)=[O:26].[CH3:29][N:30](C=O)C>>[O:26]=[S:25]1(=[O:28])[CH2:24][CH2:23][CH2:22][N:30]1[CH2:29][C:16]1[CH:17]=[CH:18][C:12]2[S:11][C:10]([N:7]3[CH2:6][CH2:5][N:4]([CH:1]([CH3:3])[CH3:2])[CH2:9][CH2:8]3)=[N:14][C:13]=2[CH:15]=1Participants
5
Procedure
To a solution of 5-aminomethyl-[2-(4-isopropylpiperazin-1-yl)benzothiazole (439 mg, 1.51 mmol) in DMF (10 mL) was added NaH (181 mg, 4.53 mmol) at 0° C. The mixture was allowed to warm to rt. After 30 min, a solution of 3-chloropropane-1-sulfonic acid (373 mg, 2.11 mmol) in DMF (1.67 mL) was added at rt. The reaction mixture was stirred at rt for 2 h and then quenched with water. The volatiles were removed and the residue was extracted with ethyl acetate. The organic extract was washed with brine and concentrated. The residue was purified by the preparative HPLC to give 267 mg (45%) of 5-(1,1-dioxo-1λ6-isothiazolidin-2-ylmethyl)-2-(4-isopropylpiperazin-1-yl)benzothiazole as a trifluoroacetate salt.
Workup
- customquenched with water
- customThe volatiles were removed
- extractionthe residue was extracted with ethyl acetate
- extractionThe organic extract
- washwas washed with brine
- concentrationconcentrated
- customThe residue was purified by the preparative HPLC
Sources & evidence
- ORD record
- ord-026b79a52eef4e8082c9941a36e728ef
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394842B2
Reaction notes
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