Potassium Hydroxide → 6-(4-Fluoro-benzyloxy)-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid

HRID 639319

Reaktionsgleichung

Reaktionsgleichung von HRID 639319
[CH2:1]([O:4][C:5]1[N:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[N:7][C:6]=1[N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[CH2:2][CH3:3].COC(C1C=NC(Cl)=C(Br)N=1)=O.[F:31][C:32]1[CH:37]=CC(CO)=[CH:34][CH:33]=1.N1CCCC1.[OH-].[K+]>>[F:31][C:32]1[CH:33]=[CH:34][C:2]([CH2:1][O:4][C:5]2[N:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[N:7][C:6]=2[N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:3][CH:37]=1

Komponenten

6

Edukt 5

HCID 14797Potassium HydroxideHCID 31268PyrrolidineHCID 680224-Fluorobenzylic alcoholHCID 59254839Methyl 6-bromo-5-chloro-2-pyrazinecarboxylateHCID 685674456-Propoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid

Produkt 1

HCID 685652886-(4-Fluoro-benzyloxy)-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acidAusbeute 13 %

Versuchsvorschrift

In analogy to the procedure described for the synthesis of 6-propoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid (example 10, step c), the title compound was synthesized from 6-bromo-5-chloro-pyrazine-2-carboxylic acid methyl ester, (4-fluoro-phenyl)-methanol (commercially available), pyrrolidine (commercially available) and subsequent saponification with KOH in 13% yield. m/z (ES+): 318.0 (M+H).

Quellen und Nachweise

ORD-Eintrag
ord-e72cafc6a78b4db198fe2c92a692d0cf
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691863B2

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