Beta-Alanine → 3-{[4-Hydroxy-7-(pyridin-2-yloxy)-isoquinoline-3-carbonyl]amino}-propionic acid

Reaktionsgleichung

CO[C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)[CH:9]=2)=[O:4].[NH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27].C[O-].[Na+]>>[OH:15][C:14]1[C:13]2[C:8](=[CH:9][C:10]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)=[CH:11][CH:12]=2)[CH:7]=[N:6][C:5]=1[C:3]([NH:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[O:4]

Komponenten

Edukt 3

HCID 239Beta-Alanine

HCID 10942334Sodium Methoxide

HCID 898129234-Hydroxy-7-(pyridin-2-yloxy)-isoquinoline-3-carboxylic acid methyl ester

Produkt 1

HCID 898129183-{[4-Hydroxy-7-(pyridin-2-yloxy)-isoquinoline-3-carbonyl]amino}-propionic acidAusbeute 76,9 %

Versuchsvorschrift

A mixture of 4-hydroxy-7-(pyridin-2-yloxy)-isoquinoline-3-carboxylic acid methyl ester (24 mg), 3-amino-propionic acid (29 mg) and NaOMe (0.48 mL, 0.5 M solution in MeOH) was microwaved at 130° C. for 1 h; then cooled, concentrated, residue was dissolved in water, acidified with 2 M HCl; solids were collected via filtration, washed with water and air dried to give the desired product (22 mg). LC MS ESI: 354 (M+1)+.