Triethylamine → 3-Chloropropane-1-sulfonic acid [2-(4-cyclopropylpiperazin-1-yl)benzothiazol-6-ylmethyl]amide
Reaction equation
[NH2:1][CH2:2][C:3]1[CH:20]=[CH:19][C:6]2[N:7]=[C:8]([N:10]3[CH2:15][CH2:14][N:13]([CH:16]4[CH2:18][CH2:17]4)[CH2:12][CH2:11]3)[S:9][C:5]=2[CH:4]=1.C(N(CC)CC)C.[Cl:28][CH2:29][CH2:30][CH2:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[CH:16]1([N:13]2[CH2:14][CH2:15][N:10]([C:8]3[S:9][C:5]4[CH:4]=[C:3]([CH2:2][NH:1][S:32]([CH2:31][CH2:30][CH2:29][Cl:28])(=[O:34])=[O:33])[CH:20]=[CH:19][C:6]=4[N:7]=3)[CH2:11][CH2:12]2)[CH2:17][CH2:18]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 6-aminomethyl-2-(4-cyclopropylpiperazin-1-yl)benzothiazole (500 mg, 1.74 mmol) in CH2Cl2 (15 mL) was added triethylamine (879 mg, 8.2 mmol). The mixture was stirred at 0° C. for 5 min and then 3-chloropropane-1-sulfonyl chloride (308 mg, 1.74 mmol) was added dropwise. The mixture was stirred at 0° C. for 1 h and then allowed gradually to reach rt. Then the mixture was stirred for another 1 h at rt. The volatiles were evaporated and the residue was extracted with CH2Cl2. This afforded a crude product, which was purified by column chromatography on silica gel (elute: 5% CH2Cl2 in methanol) to give 3-chloro-propane-1-sulfonic acid [2-(4-cyclopropylpiperazin-1-yl)benzothiazol-6-ylmethyl]amide 300 mg (39.5%).
Workup
- stirringThe mixture was stirred at 0° C. for 1 h
- customto reach rt
- stirringThen the mixture was stirred for another 1 h at rt
- customThe volatiles were evaporated
- extractionthe residue was extracted with CH2Cl2
- customThis afforded a crude product, which
- customwas purified by column chromatography on silica gel (elute: 5% CH2Cl2 in methanol)
Sources & evidence
- ORD record
- ord-c9c7793715c3471dbbe3cb3d473bc045
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772285B2
Reaction notes
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