1-Iodopentane → N-benzyl-N'-[3,5-bis(trifluoromethyl)benzoyl]-N-({4-[(pentyloxy)methyl]cyclohexyl}methyl)sulfamide

HRID 23736

Reaktionsgleichung

Reaktionsgleichung von HRID 23736
[CH2:1]([N:8]([CH2:29][CH:30]1[CH2:35][CH2:34][CH:33]([CH2:36][OH:37])[CH2:32][CH2:31]1)[S:9]([NH:12][C:13](=[O:28])[C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([C:24]([F:27])([F:26])[F:25])[CH:15]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:38]([C:42]1[CH:47]=[CH:46]C=C(C(C)(C)C)N=1)(C)(C)[CH3:39].ICCCCC>ClCCl.[O-]S(C(F)(F)F)(=O)=O.[Ag+]>[CH2:1]([N:8]([CH2:29][CH:30]1[CH2:31][CH2:32][CH:33]([CH2:36][O:37][CH2:39][CH2:38][CH2:42][CH2:47][CH3:46])[CH2:34][CH2:35]1)[S:9]([NH:12][C:13](=[O:28])[C:14]1[CH:19]=[C:18]([C:20]([F:21])([F:22])[F:23])[CH:17]=[C:16]([C:24]([F:25])([F:26])[F:27])[CH:15]=1)(=[O:11])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 123351-IodopentaneHCID 685102,6-Di-tert-butylpyridineHCID 22574483N-benzyl-N'-[3,5-bis(trifluoromethyl)benzoyl]-N-{[4-(hydroxymethyl)cyclohexyl]methyl}sulfamide

Produkt 1

HCID 22574478N-benzyl-N'-[3,5-bis(trifluoromethyl)benzoyl]-N-({4-[(pentyloxy)methyl]cyclohexyl}methyl)sulfamideAusbeute 73,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 76223Silver(I) trifluoromethanesulfonateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Intermediate (4) (27.6 mg, 50 μmole, 1.0 eq) was dissolved in dichloromethane (250 μL), after which 2,6-di-t-butyl pyridine (36 μL, 160 μmole, 3.2 eq), silver triflate (38.5 mg, 150 μmole, 3.0 eq) and iodopentane (23 μL, 175 μmole, 3.5 eq) were added. After 45 minutes the reaction mixture was directly purified to give 23 mg of the title compound. 1H NMR (500 MHz, DMSO-d6): δ 8.45 (s, 2H), 8.15 (s, 1H), 7.36 (d, 2H), 7.24 (t, 2H), 7.17 (t, 1H), 4.39 (s, 2H), 3.30 (water), 3.23 (t, 2H), 3.01 (d, 2H), 2.92 (d, 2H), 2.48 (DMSO), 1.61 (m, 2H), 1.54 (m, 2H), 1.41 (m, 2H), 1.34-1.19 (m, 6H), 0.82 (t, 3H), 0.62 (m, 4H).

Aufarbeitung

  1. customAfter 45 minutes the reaction mixture was directly purified

Quellen und Nachweise

ORD-Eintrag
ord-a8255898e3c043f2be177310735149d0
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852738B2

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