Triethylamine → HCID 178495806, Verbindung

HRID 78444

Reaktionsgleichung

Reaktionsgleichung von HRID 78444
[Cl:1][C:2]1[CH:11]=[C:10]([C:12]([OH:14])=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.ClC1C=C(C(Cl)=O)C2C(=CC=CC=2)N=1.S(Cl)(Cl)=O.[CH3:33][O:34][CH2:35][CH2:36][N:37]1[C:41]([CH3:42])=[C:40]([CH3:43])[S:39][C:38]1=[NH:44].CCN(CC)CC>C1COCC1>[Cl:1][C:2]1[CH:11]=[C:10]([C:12](/[N:44]=[C:38]2\[S:39][C:40]([CH3:43])=[C:41]([CH3:42])[N:37]\2[CH2:36][CH2:35][O:34][CH3:33])=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 754382-Chloroquinoline-4-carbonyl chloride2×HCID 2305822-Chloroquinoline-4-carboxylic acidHCID 668517233-(2-Methoxy-ethyl)-4,5-dimethyl-3H-thiazol-2-ylideneamine

Produkt 1

HCID 178495806HCID 178495806, VerbindungAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The 2-chloroquinoline-4-carboxylic acid (TCI-JP, 0.29 g, 1.4 mmol) was converted to 2-chloroquinoline-4-carbonyl chloride with 5 mL of thionyl chloride using the method described in Example 134A. The product of Example 126A (0.20 g, 1.1 mmol), Et3N (0.3 mL, 2.2 mmol) and 2-chloroquinoline-4-carbonyl chloride in 30 mL THF were processed as in Example 134B to afford the title compound (0.14 g, 0.37 mmol, 35% yield). 1H NMR (300 MHz, CD3OD) δ ppm 2.33 (s, 3H), 2.35 (s, 3H), 3.31 (s, 3H), 3.78 (t, J=5.3 Hz, 2H), 4.49 (t, J=5.3 Hz, 2H), 7.66 (ddd, J=8.5, 7.1, 1.4 Hz, 1H), 7.81 (ddd, J=8.5, 7.1, 1.4 Hz, 1H), 7.94 (s, 1H), 7.99 (dt, J=8.5, 0.7 Hz, 1H), 8.83 (dd, J=8.6, 1.2 Hz, 1H); MS (DCI/NH3) m/z 376 (M+H)+; Anal. calculated for C18H18ClN3O2S: C, 57.52; H, 4.83; N, 11.18. Found: C, 57.44; H, 4.59; N, 10.97.

Quellen und Nachweise

ORD-Eintrag
ord-8779388d2c934a159c207188d5a379bd
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841334B2

Verknüpfte Notizen

Wird geladen…