Triethylamine → N-[5-(3-{[(methylsulfonyl)amino]methyl}phenyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide

HRID 18429

Reaktionsgleichung

Reaktionsgleichung von HRID 18429
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[CH2:14][CH:13]([NH:18][S:19]([CH:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])[CH2:12]3)[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>ClCCl>[CH3:32][S:33]([NH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[CH2:14][CH:13]([NH:18][S:19]([CH:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])[CH2:12]3)[CH:6]=[CH:7][CH:8]=1)(=[O:35])=[O:34]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11515729N-{5-[3-(aminomethyl)phenyl]-2,3-dihydro-1H-inden-2-yl}-2-propanesulfonamide

Produkt 1

HCID 11669000N-[5-(3-{[(methylsulfonyl)amino]methyl}phenyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamideAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of N-{5-[3-(aminomethyl)phenyl]-2,3-dihydro-1H-inden-2-yl}-2-propanesulfonamide (69 mg, 0.2 mmol) in dichloromethane (5 ml) was treated with triethylamine (40 mg, 0.4 mmol), followed by methanesulfonyl chloride (25 mg, 0.22 mmol) and the wole mix stirred at room temperature under argon for 1 h. The reaction mix was washed with 0.5M hydrochloric acid, and the organic layer was evaporated under reduced pressure to give a brown oil which was purified by column chromatography on a 1 g SCX column eluting from 0-50% ethyl acetate in 40-60° C. petroleum ether to give the title compound as a yellow oil (46 mg, 55%).

Aufarbeitung

  1. additionthe wole mix
  2. additionThe reaction mix
  3. washwas washed with 0.5M hydrochloric acid
  4. customthe organic layer was evaporated under reduced pressure
  5. customto give a brown oil which
  6. customwas purified by column chromatography on a 1 g SCX column
  7. washeluting from 0-50% ethyl acetate in 40-60° C. petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-8db9dd41d11c4b72a71329da174e1868
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741351B2

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