Pyrrolidine → HCID 89781942, Verbindung

Reaktionsgleichung

[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([OH:14])=O)[CH:8]=[CH:7]2.C(Cl)(=O)C(Cl)=O.[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([N:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:14])[CH:8]=[CH:7]2

Komponenten

Edukt 3

HCID 31268Pyrrolidine

HCID 65578Oxalyl chloride

HCID 336959058-Bromoquinoline-2-carboxylic acid

Produkt 1

HCID 89781942HCID 89781942, VerbindungAusbeute 94,2 %

Versuchsvorschrift

This compound (365 mg, 94% yield) as a tan crystalline solid was prepared similarly to that described in Example 167a, using 8-bromoquinoline-2-carboxylic acid (Princeton BioMolecular Research, Monmouth Junction, N.J.; 320 mg, 1.27 mmol), oxalyl chloride (2.54 mmol), and pyrrolidine (0.10 mL, 1.27 mmol) as starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.59 (1H, d, J=8.4 Hz), 8.23 (1H, dd, J=7.6, 1.2 Hz), 8.11 (1H, dd, J=8.2, 1.0 Hz), 8.01 (1H, d, J=8.6 Hz), 7.63 (1H, t, J=7.8 Hz), 3.98 (2H, t, J=6.5 Hz), 3.61 (2H, t, J=6.5 Hz), 1.95 (4H, m). m/z (ESI, +ve) 307/307 (M+H)+.