Chloroacetyl chloride → HCID 178459410, Verbindung

HRID 402682

Reaktionsgleichung

Reaktionsgleichung von HRID 402682
C(O[C:5]1[O:6][CH2:7][C:8](=[O:16])[C:9]=1[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])(C)C.C(OC(C)C)(=O)CC(OC(C)C)=O.ClCC(Cl)=O.[CH3:35][NH:36][CH2:37][C:38]1[S:39][CH:40]=[CH:41][CH:42]=1.C(N(CC)CC)C.[NH:50]1[C:58]2[C:53](=[CH:54][CH:55]=[CH:56][N:57]=2)[C:52]([CH:59]=O)=[CH:51]1>CC(O)C>[NH:50]1[C:58]2=[N:57][CH:56]=[CH:55][CH:54]=[C:53]2[C:52]([CH:59]=[C:7]2[O:6][C:5]([N:36]([CH3:35])[CH2:37][C:38]3[S:39][CH:40]=[CH:41][CH:42]=3)=[C:9]([C:10]([O:12][CH:13]([CH3:14])[CH3:15])=[O:11])[C:8]2=[O:16])=[CH:51]1

Komponenten

8

Edukt 6

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 83223Diisopropyl malonateHCID 436153N-Methyl-1-(thiophen-2-yl)methanamineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 51050080Isopropyl 2-isopropoxy-4-oxo-4,5-dihydrofuran-3-carboxylate

Produkt 1

HCID 178459410HCID 178459410, VerbindungAusbeute 18,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A solution of isopropyl 2-isopropoxy-4-oxo-4,5-dihydrofuran-3-carboxylate (0.10 g, 0.44 mmol) which similarly prepared according to the procedure described in the Example 74, Third step using diisopropyl malonate and chloroacetyl chloride, N-methyl-N-(2-thienylmethyl)amine (0.061 mg, 0.048 mmol) and triethylamine (0.18 mL, 1.3 mmol) in 2-propanol (2.0 mL) was stirred for 7 days then refluxed for further 24 h. To this reaction mixture, 7-azaindole-3-carboxaldehyde (0.065 g, 0.44 mmol) was added then the mixture was refluxed for 24 h. Cooled to ambient temperature, the reaction mixture was purified by preparative HPLC to afford the titled compound as solid (0.0038 g, y. 2%).

Aufarbeitung

  1. temperaturethen refluxed for further 24 h
  2. temperaturethe mixture was refluxed for 24 h
  3. customthe reaction mixture was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-a0db90cdd92a4033986137cc6682d75b
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742113B2

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