Triethylamine → 3-Chloropropane-1-sulfonic acid [2-(4-cyclopropyl-piperazin-1-yl)benzooxazol-5-ylmethyl]amide
Reaction equation
[CH:1]1([N:4]2[CH2:9][CH2:8][N:7]([C:10]3[O:11][C:12]4[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=4[N:14]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.C[CH2:20][N:21](CC)CC.[Cl:26][CH2:27][CH2:28][CH2:29][S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl>[CH:1]1([N:4]2[CH2:9][CH2:8][N:7]([C:10]3[O:11][C:12]4[CH:18]=[CH:17][C:16]([CH2:20][NH:21][S:30]([CH2:29][CH2:28][CH2:27][Cl:26])(=[O:32])=[O:31])=[CH:15][C:13]=4[N:14]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 5-aminomethyl-[2-(4-cyclopropylpiperazin-1-yl)benzooxazole (500 mg, 1.84 mmol) in CH2Cl2 (15 mL) was added Et3N (929 mg, 9.2 mmol). The mixture was stirred at 0° C. for 5 min and then 3-chloropropane-1-sulfonyl chloride (326 mg, 1.84 mmol) was added dropwise. The mixture was stirred at 0° C. for 1 h and brought gradually to rt. Then the mixture was stirred for another 1 h. The volatiles were removed and the residue was extracted with CH2Cl2. The resulting residue was purified by column chromatography on silica gel (elute: 5% CH2Cl2 in methanol) to give 3-chloropropane-1-sulfonic acid [2-(4-cyclopropylpiperazin-1-yl)benzooxazol-5-ylmethyl]amide (315 mg, 42%).
Workup
- stirringThe mixture was stirred at 0° C. for 1 h
- custombrought gradually to rt
- stirringThen the mixture was stirred for another 1 h
- customThe volatiles were removed
- extractionthe residue was extracted with CH2Cl2
- customThe resulting residue was purified by column chromatography on silica gel (elute: 5% CH2Cl2 in methanol)
Sources & evidence
- ORD record
- ord-2d193ea6640549a2943880f9ee829a0b
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394842B2
Reaction notes
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