Benzenamine, 3-(methylthio)- → HCID 90022642, compound

HRID 1772898Notes

Reaction equation

HRID 1772898 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].[Cl:22][C:23]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:24]=1[CH2:25][NH2:26]>O1CCOCC1.CC#N>[Cl:22][C:23]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:24]=1[CH2:25][NH:26][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[S:9]([NH:18][C:17]1[CH:19]=[CH:20][CH:21]=[C:15]([S:14][CH3:13])[CH:16]=1)(=[O:11])=[O:10]

Participants

6

Reactant 3

HCID 15693Benzenamine, 3-(methylthio)-HCID 848332-Chloro-6-fluorobenzylamineHCID 27369112,5-Difluorobenzenesulfonyl chloride

Product 1

HCID 90022642HCID 90022642, compoundYield 5.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

The title compound (119 mg, 0.26 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 2-chloro-6-fluorobenzyl amine (762 uL, 5.9 mmol) in MeCN (1.5 mL) at 180° C. in a Biotage Initiator microwave reactor using the methods of (IntB1).

Sources & evidence

ORD record
ord-e21174be3c954af7bc29d2e2b1668e16
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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