Triethylamine → HCID 67819556, compound

HRID 925295Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:10]=[C:9]([CH2:11][NH2:12])[N:8]=[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:6]=1)(=[O:4])=[O:3].C(N(CC)CC)C.[Cl:26][C:27]1[S:31][C:30]([S:32](Cl)(=[O:34])=[O:33])=[CH:29][CH:28]=1>C(Cl)Cl>[CH3:1][S:2]([C:5]1[CH:10]=[C:9]([CH2:11][NH:12][S:32]([C:30]2[S:31][C:27]([Cl:26])=[CH:28][CH:29]=2)(=[O:34])=[O:33])[N:8]=[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:6]=1)(=[O:3])=[O:4]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of C-(4-Methanesulfonyl-[2,2′]bipyridinyl-6-yl)-methylamine (40.0 mg, 0.153 mmol), triethylamine (58.0 μL, 0.459 mmol), 5-chlorothiophene-2-sulfonyl chloride (42.0 mg, 0.184 mmol) and DCM (2 mL) was stirred at 25° C. for 2 hours. The reaction mixture was concentrated under reduced pressure and the crude purified by column chromatography on silica gel (0-10% methanol in dichloromethane) to afford 5-chloro-thiophene-2-sulfonic acid (4-methanesulfonyl-[2,2′]bipyridinyl-6-ylmethyl)-amide as a white solid (20.0 mg, 30%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe crude purified by column chromatography on silica gel (0-10% methanol in dichloromethane)

Sources & evidence

ORD record: ord-dbc50ec3702a4645b51829a938392285
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284296B2

Reaction notes

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