Triethylamine → N-[3-(4',5'-difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-phenyl]-methanesulfonamide

HRID 547863Notes

Reaction equation

HRID 547863 reaction equation
Cl.[F:2][C:3]1[C:8]([F:9])=[CH:7][C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:19]=[C:20]([NH2:24])[CH:21]=[CH:22][CH:23]=3)=[CH:12][CH:11]=2)=[C:5]([O:25][CH3:26])[CH:4]=1.C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36].FC1C=C(F)C(F)=CC=1C1C=CC(OCC2C=C(NS(C)(=O)=O)C=CC=2)=CC=1>N1C=CC=CC=1>[F:2][C:3]1[C:8]([F:9])=[CH:7][C:6]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:17][C:18]3[CH:19]=[C:20]([NH:24][S:35]([CH3:34])(=[O:37])=[O:36])[CH:21]=[CH:22][CH:23]=3)=[CH:14][CH:15]=2)=[C:5]([O:25][CH3:26])[CH:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 52920349N-[3-(2',4',5'-trifluoro-biphenyl-4-yloxymethyl)-phenyl]-methanesulfonamideHCID 67153767HCID 67153767, compound

Product 1

HCID 52920467N-[3-(4',5'-difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-phenyl]-methanesulfonamideYield 53.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-phenylamine hydrochloride (101 mg, 0.269 mmol), triethylamine (38 uL, 0.269 mmol) and methanesulfonyl chloride (27 uL, 0.349 mmol) in dry pyridine (4 mL) was reacted similar to N-[3-(2′,4′,5′-trifluoro-biphenyl-4-yloxymethyl)-phenyl]-methanesulfonamide above. The crude product was purified by flash chromatography with a 0-15% gradient of ethyl acetate in hexanes to yield 60 mg of N-[3-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-phenyl]-methanesulfonamide as a white solid. LC-MS (ES) calculated for C21H19F2NO4S, 419.45; found m/z 418 [M−H]−.

Workup

  1. customThe crude product was purified by flash chromatography with a 0-15% gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-d6c5785be2a5470790e703fb0caf2a6a
Source dataset
uspto-grants-2011_05
Patent number
US07939569B1

Reaction notes

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