Methanesulfonyl chloride → [(Methylethyl)sulfonyl][2-(4-{3-[(methylsulfonyl)amino]propyl}phenyl)propyl]amine

HRID 48376Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:20])[CH2:12][NH:13][S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:7][CH:6]=1.[CH3:21][S:22](Cl)(=[O:24])=[O:23].C1CCN2C(=NCCC2)CC1>>[CH3:18][CH:17]([S:14]([NH:13][CH2:12][CH:11]([C:8]1[CH:7]=[CH:6][C:5]([CH2:4][CH2:3][CH2:2][NH:1][S:22]([CH3:21])(=[O:24])=[O:23])=[CH:10][CH:9]=1)[CH3:20])(=[O:16])=[O:15])[CH3:19]

Participants

Reactant 3

HCID 31297Methanesulfonyl chloride

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

HCID 22743228{2-[4-(3-Aminopropyl)phenyl]propyl}[(methylethyl)sulfonyl]amine

Product 1

HCID 12991221[(Methylethyl)sulfonyl][2-(4-{3-[(methylsulfonyl)amino]propyl}phenyl)propyl]amineYield 24%

Procedure

Scheme Vc, step C: {2-[4-(3-aminopropyl)phenyl]propyl}[(methylethyl)sulfonyl]amine (0.5 g, 1.67 mmol), methanesulfonyl chloride (0.15 mL, 1.84 mmol) and DBU (0.29 mL, 1.93 mmol) were combined and sulfonylation was carried out in a manner analogous to the procedure described in example 2 to provide the final title compound, [(methylethyl)sulfonyl][2-(4-{3-[(methylsulfonyl)amino]propyl}phenyl)propyl]amine, (0.15 g, 24%) as a white crystalline solid. Electron spray M.S. 377 (M*+H). Analysis for C16H28N2O4S2:

Sources & evidence

ORD record: ord-7ccb4de3b5ea46b7bcfba2e7ae03c9fd
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06703425B2

Reaction notes

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