Methanesulfonyl chloride → [(2-Fluoro-4-{2-[(methylsulfonyl)amino]ethyl}phenyl)methyl](methylsulfonyl)amine

HRID 48367Notes

Reaction equation

HRID 48367 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH2:11])=[CH:5][C:4]=1[F:12].[CH3:13][S:14](Cl)(=[O:16])=[O:15].C1CCN2C(=NCCC2)CC1>>[F:12][C:4]1[CH:5]=[C:6]([CH2:9][CH2:10][NH:11][S:14]([CH3:13])(=[O:16])=[O:15])[CH:7]=[CH:8][C:3]=1[CH2:2][NH:1][S:14]([CH3:13])(=[O:16])=[O:15]

Participants

4

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 129912342-[4-(Aminomethyl)-3-fluorophenyl]ethylamine

Product 1

HCID 12991397[(2-Fluoro-4-{2-[(methylsulfonyl)amino]ethyl}phenyl)methyl](methylsulfonyl)amineYield 37%

Procedure

2-[4-(Aminomethyl)-3-fluorophenyl]ethylamine (0.3 g, 1.25 mmol) was combined with methanesulfonyl chloride (0.2 mL, 2.75 mmol), and DBU (1 mL, 3.12 mmol) in a manner analogous to the procedure described in example 2 to provide the final title compound, [(2-fluoro-4-{2-[(methylsulfonyl)amino]ethyl}phenyl)methyl](methylsulfonyl)amine, (0.15 g, 37%) as a white crystalline solid. Electron spray M.S. 323 (M*−H). Analysis for C11H17FN2O4S2:

Sources & evidence

ORD record
ord-21f9f6c6a8c244b29bb3e9f92882055a
Source dataset
uspto-grants-2004_03
Patent number
US06703425B2

Reaction notes

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