Ethanesulfonyl chloride → HCID 86618572, compound

HRID 2370578Notes

Reaction equation

Cl.[CH3:2][O:3][C:4]1[CH:19]=[CH:18][C:7]2[N:8]=[C:9]([NH:11][C@H:12]3[CH2:17][CH2:16][CH2:15][NH:14][CH2:13]3)[S:10][C:6]=2[CH:5]=1.[CH2:20]([S:22](Cl)(=[O:24])=[O:23])[CH3:21].CCN(C(C)C)C(C)C>CN1C(=O)CCC1.O.C(OCC)(=O)C>[CH2:20]([S:22]([N:14]1[CH2:15][CH2:16][CH2:17][C@H:12]([NH:11][C:9]2[S:10][C:6]3[CH:5]=[C:4]([O:3][CH3:2])[CH:19]=[CH:18][C:7]=3[N:8]=2)[CH2:13]1)(=[O:24])=[O:23])[CH3:21]

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of (S)-6-methoxy-N-(piperidin-3-yl)benzo[d]thiazol-2-amine hydrochloride salt (2.0 g, 5.95 mmol), ethylsulfonyl chloride (1.13 ml, 11.91 mmol) and DIPEA (4.11 ml, 23.8 mmol) in NMP (25 ml) was heated at 55° C. for 16 hours 50 min. The reaction mixture was allowed to cool down to room temperature and diluted with water (150 ml) and ethyl acetate (150 ml). After stirring vigorously for 1 hour the separated organic layer was washed with water (3×100 ml), saturated sodium bicarbonate solution (3×100 ml), water (100 ml) and brine (100 ml) and dried over sodium sulfate. Concentration in vacuo and purification by flash chromatography over silica gel with ethyl acetate:hexane (20:80-100:0) provided (S)—N-(1-(ethylsulfonyl)piperidin-3-yl)-6-methoxybenzo[d]thiazol-2-amine as tan solid. Yield: 1.22 g. ES/MS m/z 356.0 (MH+), Rt=2.12 min.

Workup

temperatureto cool down to room temperature
washwas washed with water (3×100 ml), saturated sodium bicarbonate solution (3×100 ml), water (100 ml) and brine (100 ml)
dry with materialdried over sodium sulfate
concentrationConcentration
customin vacuo and purification by flash chromatography over silica gel with ethyl acetate:hexane (20:80-100:0)

Sources & evidence

ORD record: ord-d6f7380917cf46178badfa64272dab46
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710048B2

Reaction notes

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