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

HRID 48380Notes

Reaction equation

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

Participants

Reactant 3

HCID 31297Methanesulfonyl chloride

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

HCID 22743208{2-[4-(2-Aminoethyl)phenyl]propyl}[(methylethyl)sulfonyl]amine

Product 1

HCID 22743264[(Methylethyl)sulfonyl][2-(4-{2-[(methylsulfonyl)amino]ethyl}phenyl)propyl]amineYield 78.1%

Procedure

Scheme Va, step C: {2-[4-(2-Aminoethyl)phenyl]propyl}[(methylethyl)sulfonyl]amine (0.15 g, 0.53 mmol), methanesulfonyl chloride (0.1 mL, 0.58 mmol) and DBU (0.1 mL, 0.61 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-{2-[(methylsulfonyl)amino]ethyl}phenyl)propyl]amine, (0.15 g, 78%) as a white crystalline solid. Electron spray M.S. 363 (M*+H). Analysis for C15H26N2O4S2:

Sources & evidence

ORD record: ord-e98e6338c3b7463bae2fec2e3e19c363
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06703425B2

Reaction notes

Loading…