Triethylamine → (R)-(7-Chlorothieno[3,2-b]pyridin-2-yl)(3-(dimethylamino)pyrrolidin-1-yl)methanone

HRID 1825097Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1825097
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([O-:13])=O)[S:10][C:3]=12.[Li+].S(Cl)(Cl)=O.[CH3:19][N:20]([CH3:26])[C@@H:21]1[CH2:25][CH2:24][NH:23][CH2:22]1.CCN(CC)CC>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:23]3[CH2:24][CH2:25][C@@H:21]([N:20]([CH3:26])[CH3:19])[CH2:22]3)=[O:13])[S:10][C:3]=12

Komponenten

5

Edukt 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 2758521(3R)-(+)-3-(Dimethylamino)pyrrolidineHCID 23677819Lithium 7-chlorothieno[3,2-b]pyridine-2-carboxylate

Produkt 1

HCID 20745989(R)-(7-Chlorothieno[3,2-b]pyridin-2-yl)(3-(dimethylamino)pyrrolidin-1-yl)methanoneAusbeute 43,3 %

Versuchsvorschrift

This material was prepared from lithium 7-chlorothieno[3,2-b]pyridine-2-carboxylate (0.214 g, 1.0 mmole) by treatment with thionyl chloride followed by reaction of the resultant acyl chloride with (3R)-N,N-dimethylpyrrolidin-3-amine (0.114 g, 1.0 mmole) and Et3N (0.139 ml, 1.0 mmole), in a manner as previously described for example 9d to give a brown solid (0.134 g, 43%). 1H NMR (300 MHz, CD3OD) δ σ7.24 (1H, d, J=5.1 Hz), 6.57 (1H, d, J=8.48 Hz), 6.15 (1H, d, J=5.1 Hz), 2.70 (1H, m), 2.51 (2H, m), 2.24 (1H, m), 2.04 (1H, m), 1.49 (1H, m), 0.93 (3H, s), 0.90 (3H, s), 0.52 (1H, m); ESIMS (MH+): 310.10.

Quellen und Nachweise

ORD-Eintrag
ord-4a303500952b462eac4d224695fdac9d
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07045528B2

Notizen zur Reaktion

Wird geladen…