Benzenesulfonyl chloride → HCID 11306401, compound

HRID 855582Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH:11]([OH:24])[CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]3[S:21][C:20]([CH3:22])=[N:19][C:18]=3[CH:23]=2)[CH2:6][CH2:5]1.[C:25]1([S:31](Cl)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>COCCOC>[OH:24][C@@H:11]([CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]2[S:21][C:20]([CH3:22])=[N:19][C:18]=2[CH:23]=1)[CH2:10][N:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][NH:1][S:31]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:33])=[O:32])[CH2:5][CH2:6]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1-[4-(2-aminoethyl)piperazinyl]-3-(2-methylbenzothiazol-5-yloxy)propan-2-ol (60 mg, 0.171 mmol) in DME (6 mL) was cooled to 0° C. and benzene sulfonyl chloride (0.022 mL, 0.172 mmol) was added. The solution was stirred at 0° C. for 5 min and then at RT for 10 min. The reaction mixture was concentrated to an oil and purified via flash column chromatography (9:1 CHCl3/MeOH) to afford (2-{4-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperazinyl}ethyl) (phenylsulfonyl)amine.

Workup

waitat RT for 10 min
concentrationThe reaction mixture was concentrated to an oil
custompurified via flash column chromatography (9:1 CHCl3/MeOH)

Sources & evidence

ORD record: ord-374af11705ad4834ae8116e74f5758ae
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262198B2

Reaction notes

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