Triethylamine → HCID 178514734, Verbindung

HRID 333116

Reaktionsgleichung

Reaktionsgleichung von HRID 333116
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)=[C:2]=[S:3].[CH2:14]([N:16](CC)CC)[CH3:15].FC(F)(F)C([O-])=O.[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH2:34][N:35]([CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=1)[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]N.[C:50](=[Re+:52](=[C:55]=[O:56])=[C:53]=[O:54])=[O:51]>C(#N)C>[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH2:34][N:35]([CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=1)[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:15][CH2:14][NH:16][C:2](=[S:3])[NH:1][C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH2:13])(=[O:11])=[O:12])=[CH:8][CH:9]=1.[C:50](=[Re+:52](=[C:55]=[O:56])=[C:53]=[O:54])=[O:51]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 5213594-IsothiocyanatobenzenesulfonamideHCID 178510988HCID 178510988, Verbindung

Produkt 1

HCID 178514734HCID 178514734, VerbindungAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a suspension of 4-isothiocyanatobenzenesulfonamide (11 mg, 0.05 mmol) in dry acetonitrile (1 mL) and triethylamine (15 μL, 0.11 mmol) was added tricarbonyl rhenium(I) 6-(bis(pyridin-2-ylmethyl)amino)hexylamine trifluoroacetate (40 mg, 0.48 mmol). The reaction mixture was stirred for 3 h at room temperature. The reaction mixture was concentrated and the resulting solid recrystallized from methanol/water to afford MIP-1140 as an off-white solid (38 mg, 96%). 1H NMR (400 MHz, DMSO-d6) δ 9.83 (br, 1H), 8.80 (d, J=5.4 Hz, 2H), 8.11 (br, 1H), 7.96 (m, 2H), 7.86-7.25 (m, 10H), 4.90 (m, 4H) 3.72 (m, 2H), 3.47 (br, 2H), 1.83 (br, 2H), 1.57 (m, 2H), 1.37 (bm, 8H); (M+H)+ (811).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customthe resulting solid recrystallized from methanol/water

Quellen und Nachweise

ORD-Eintrag
ord-08ed7f9128194642b60b3f784d72eb49
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877970B2

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