2,9-Dimethyl-1,10-phenanthroline → 2-Amino-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-isonicotinic acid pentyl ester

HRID 1984604Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1984604
CC1C=CC2C=CC3C=CC(C)=NC=3C=2N=1.[CH2:17]([O:22][C:23](=[O:32])[C:24]1[C:29](I)=[CH:28][N:27]=[C:26]([NH2:31])[CH:25]=1)[CH2:18][CH2:19][CH2:20][CH3:21].[N:33]1([S:39]([C:42]2[CH:47]=[CH:46][C:45]([SH:48])=[CH:44][CH:43]=2)(=[O:41])=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.[Cu](I)I>[CH2:17]([O:22][C:23](=[O:32])[C:24]1[C:29]([S:48][C:45]2[CH:44]=[CH:43][C:42]([S:39]([N:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)(=[O:40])=[O:41])=[CH:47][CH:46]=2)=[CH:28][N:27]=[C:26]([NH2:31])[CH:25]=1)[CH2:18][CH2:19][CH2:20][CH3:21]

Komponenten

7

Edukt 4

HCID 652372,9-Dimethyl-1,10-phenanthrolineHCID 23676156Sodium t-butoxideHCID 57718193HCID 57718193, VerbindungHCID 577182904-(N-piperidinylsulfonyl)thiophenol

Produkt 1

HCID 577182132-Amino-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-isonicotinic acid pentyl esterAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Copper iodide (26 mg, 0.14 mmol) and neocuproine (29 mg, 0.14 mmol) were added to a stirred mixture of 2-amino-5-iodo-isonicotinic acid pentyl ester (450 mg, 1.35 mmol), 4-(piperidine-1-sulfonyl)-benzenethiol (449 mg, 1.49 mmol) and sodium t-butoxide (195 mg, 2.025 mmol) in toluene (10 ml) and the reaction was heated to reflux overnight. The reaction was cooled to room temperature, solids filtered off through celite and the filtrate concentrated under reduced pressure onto silica. The residue was purified by flash column chromatography using ethyl acetate 2/3 hexane as eluent to afford 2-amino-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-isonicotinic acid pentyl ester as an orange solid (348 mg, 56%). 1H NMR (CDCl3): (1H, s, py); 7.51 (2H, d, Ar); 7.10 (2H, d, Ar); 6.80 (1H, s, py); 4.92 (2H, br s, NH2); 4.14 (2H, t, OCH2); 2.90 (4H, m, 2×CH2N pip); 1.53 (6H, m, OCH2CH2, 2×CH2 pip); 1.46 (2H, m, CH2 pip); 1.24 (4H, m, OCH2CH2CH2CH2CH3); 0.80 (3H, t, CH2CH3).

Aufarbeitung

  1. temperaturethe reaction was heated
  2. temperatureto reflux overnight
  3. filtrationsolids filtered off through celite
  4. concentrationthe filtrate concentrated under reduced pressure onto silica
  5. customThe residue was purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8e1046b6e9b44611a5aae62713ac15c6
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544702B2

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