Sodium triacetoxyborohydride → HCID 68430759, Verbindung

HRID 2090244Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2090244
[CH:1]([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:7][CH:8]=1)=O.[NH2:14][CH2:15][CH2:16][CH2:17][N:18]1[C:30]2[C:29]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N:23]=[C:22]([NH2:31])[C:21]=2[N:20]=[C:19]1[CH2:32][O:33][CH2:34][CH3:35].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[NH2:31][C:22]1[C:21]2[N:20]=[C:19]([CH2:32][O:33][CH2:34][CH3:35])[N:18]([CH2:17][CH2:16][CH2:15][NH:14][CH2:1][C:3]3[CH:4]=[C:5]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:7][CH:8]=3)[C:30]=2[C:29]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[N:23]=1

Komponenten

5

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 11819590Methyl 2-(3-formylphenyl)acetateHCID 223444341-(3-Aminopropyl)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-4-amine

Produkt 1

HCID 68430759HCID 68430759, VerbindungAusbeute 4,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl 2-(3-formylphenyl)acetate (199 mg) was added to the product of step (iv) (334 mg) in THF (20 mL) at 25° C. under nitrogen. The resulting solution was stirred at rt for 6 h. Sodium triacetoxyborohydride (1183 mg) was added to the reaction mixture at rt under nitrogen and the mixture was stirred at rt for 15 h. The reaction mixture was quenched with water and dissolved in MeOH. The product was purified via RPHPLC, which afforded 25 mg of the desired product as a white solid.

Aufarbeitung

  1. stirringthe mixture was stirred at rt for 15 h
  2. customThe reaction mixture was quenched with water
  3. dissolutiondissolved in MeOH
  4. customThe product was purified via RPHPLC, which

Quellen und Nachweise

ORD-Eintrag
ord-fb66db14b3e14294a64d61579d88dee1
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436178B2

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