Triethylamine → HCID 67819585, compound

HRID 925290Notes

Reaction equation

HRID 925290 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH2:10])[N:6]=[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:4]=1.C(N(CC)CC)C.[F:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1>ClCCl>[F:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([NH:10][CH2:9][C:7]2[N:6]=[C:5]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=2)(=[O:33])=[O:32])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 67608342HCID 67608342, compound

Product 1

HCID 67819585HCID 67819585, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of C-(4-Methoxy-[2,2′]bipyridinyl-6-yl)-methylamine (62.0 mg, 0.29 mmol), triethylamine (55.1 μL, 0.43 mmol), 4-Fluoro-benzenesulfonyl chloride (72.0 mg, 0.371 mmol) and dichloromethane (3 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 (0-100% Ethyl acetate in Hexane) to afford 4-Fluoro-N-(4-methoxy-[2,2′]bipyridinyl-6-ylmethyl)-benzenesulfonamide as a white solid (48.1 mg, 38%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe crude purified by column chromatography on silica gel (0-100% Ethyl acetate in Hexane)

Sources & evidence

ORD record
ord-52a2fe0c2b1f4e86a7f2c8b964d5fd5b
Source dataset
uspto-grants-2016_03
Patent number
US09284296B2

Reaction notes

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