Benzenamine, 3-(methylthio)- → 5-Fluoro-2-{[1-(2-fluorophenyl)ethyl]amino}-N-[3-(methylsulfanyl)phenyl]benzenesulfonamide

HRID 1772897Notes

Reaction equation

HRID 1772897 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[S:9](Cl)(=[O:11])=[O:10].[CH3:13][S:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH2:18].[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH:29]([NH2:31])[CH3:30]>O1CCOCC1.CC#N>[F:8][C:5]1[CH:6]=[CH:7][C:2]([NH:31][CH:29]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[F:22])[CH3:30])=[C:3]([S:9]([NH:18][C:17]2[CH:19]=[CH:20][CH:21]=[C:15]([S:14][CH3:13])[CH:16]=2)(=[O:11])=[O:10])[CH:4]=1

Participants

6

Reactant 3

HCID 15693Benzenamine, 3-(methylthio)-HCID 27369112,5-Difluorobenzenesulfonyl chlorideHCID 2782361(1R)-1-(2-Fluorophenyl)ethylamine

Product 1

HCID 900303845-Fluoro-2-{[1-(2-fluorophenyl)ethyl]amino}-N-[3-(methylsulfanyl)phenyl]benzenesulfonamideYield 8.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

The title compound (139 mg, 0.32 mmol) was prepared in two steps from 2,5-difluorobenzenesulfonyl chloride (1.07 g, 5.0 mmol) and 3-(methylsulfanyl)aniline (769 mg, 5.5 mmol) in 1,4-dioxane at 70° C.; followed by 1-(2-fluorophenyl)ethanamine (500 mg, 3.6 mmol) in MeCN (0.5 mL) at 200° C. in a Biotage Initiator microwave reactor using the methods of (IntB1).

Sources & evidence

ORD record
ord-1c22ca3572394f26985373cf756652b7
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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