Lithium Hydroxide → HCID 89451654, Verbindung

HRID 526043

Reaktionsgleichung

Reaktionsgleichung von HRID 526043
[CH3:1][C:2]1[C:11]2[N:10]3[CH:12]=[CH:13][CH:14]=[C:9]3[C:8](=[O:15])[N:7]([CH2:16][C:17]([O:19]C)=[O:18])[C:6]=2[N:5]=[CH:4][CH:3]=1.[Li+].[OH-]>CO.O.C1COCC1>[CH3:1][C:2]1[C:11]2[N:10]3[CH:12]=[CH:13][CH:14]=[C:9]3[C:8](=[O:15])[N:7]([CH2:16][C:17]([OH:19])=[O:18])[C:6]=2[N:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 89451658Methyl 2-(1-methyl-6-oxopyrido[2,3-e]pyrrolo[1,2-a]pyrazin-5(6H)-yl)acetate

Produkt 1

HCID 89451654HCID 89451654, VerbindungAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

Methyl 2-(1-methyl-6-oxopyrido[2,3-e]pyrrolo[1,2-a]pyrazin-5(6H)-yl)acetate (517 mg, 1.91 mmol) was dissolved in 20 mL of MeOH/H2O/THF (1:1:4). LiOH (68.5 mg, 2.86 mmol) was added. The mixture was stirred at room temperature for 16 hours. The solvents were removed and residue was dissolved in water, washed with ether, then neutralized with 2N HCl to pH=3. 356 mg (73%) white solid was obtained after filtration and dried under vacuum. 1H NMR (400 MHz, DMSO) δ 12.90 (s, 1H), 8.27-8.17 (m, 2H), 7.29-7.19 (m, 2H), 6.80 (dd, J=2.9, 3.9 Hz, 1H), 5.02 (s, 2H), 2.85 (s, 3H). 13C NMR (101 MHz, DMSO, APT) δ 169.8, 154.5, 143.1, 141.4, 135.9, 123.9, 123.3, 122.8, 119.5, 113.3, 112.7, 41.6, 22.2. HRMS (m/z): calcd for C13H12N3O3 (M+H) 258.0879. found 258.0894.

Aufarbeitung

  1. customThe solvents were removed
  2. dissolutionresidue was dissolved in water
  3. washwashed with ether

Quellen und Nachweise

ORD-Eintrag
ord-5b470fee8d3647829d7ebdd2eea241df
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09345703B2

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