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Pyridine → HCID 69832975, Verbindung

HRID 370041
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 370041
[CH2:1]([O:3][C:4](=[O:31])[N:5]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C@H:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([O:16][CH3:17])[CH:14]=2)[N:9]([C:20](Cl)=[O:21])[C@@H:8]([CH3:23])[CH2:7]1)[CH3:2].[N:32]1[CH:37]=CC=C[CH:33]=1.Cl.CNC.[OH-].[K+]>ClCCl.C(OCC)(=O)C.O>[CH2:1]([O:3][C:4](=[O:31])[N:5]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C@H:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([O:16][CH3:17])[CH:14]=2)[N:9]([C:20](=[O:21])[N:32]([CH3:37])[CH3:33])[C@@H:8]([CH3:23])[CH2:7]1)[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 1049PyridineHCID 10473Dimethylamine, hydrochlorideHCID 14797Potassium HydroxideHCID 88014990HCID 88014990, Verbindung

Produkt 1

HCID 69832975HCID 69832975, VerbindungAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962
Water
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of cis-4-benzyl-(1-chlorocarbonyl-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl)-carbamic acid ethyl ester (Example 107A) (38 mg, 0.085 mmol), pyridine (0.5 mL), and dimethylamine hydrochloride (12 mg, 0.14 mmol) in anhydrous dichloromethane (1 mL) was stirred at room temperature overnight. Then, 10 mL water and 10 mL 2N KOH were added followed by extration with ethyl acetate (3×10 mL). The combined organic phases were washed with 1N HCl (2×10 mL), 10 mL of a saturated sodium bicarbonate solution, and 10 ml of brine. The combined washed organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. Purification by silica gel chromatography using 0-75% ethyl acetate/hexanes as eluent afforded cis-benzyl-(1-dimethylcarbamoyl-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl)-carbamic acid ethyl ester (Example 108A) (10 mg, 24%) MS m/z 455 (M+), 277 (M+ -178); 1H NMR (CDCl3) δ 3.79 (C6/7, s, 3H), 3.70 (C6/7, s, 3H), 2.79 (N1, s, 6H); and cis-benzyl-[6,7-dimethoxy-2-methyl-1-(5-oxo-penta-1,3-dienylcarbamoyl)-1,2,3,4-tetrahydro-quinolin-4-yl]-carbamic acid ethyl ester (Example 108B) (7 mg, 15%): MS m/z 508 (M+ +1), 329 (M+ -178); 1H NMR (CDCl3) δ 9.46 (aldehyde, d, 1H), 3.85 (C6/7, s, 3H), 3.79 (C6/7, s, 3H).

Aufarbeitung

  1. washThe combined organic phases were washed with 1N HCl (2×10 mL), 10 mL of a saturated sodium bicarbonate solution, and 10 ml of brine
  2. washThe combined washed organic extracts
  3. dry with materialwere dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-75ea8d9146a0442faf47a7b2f3dcb8a9
Quelldatensatz
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06140342

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