StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

2-Chloronicotinic acid → 2-Chloro-N-[1-(2,6-dichloro-pyridin-3-yl)-cyclopropylmethyl]nicotinamide

HRID 578877
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 578877
[Cl:1][C:2]1[C:7]([C:8]2([CH2:11][NH2:12])[CH2:10][CH2:9]2)=[CH:6][CH:5]=[C:4]([Cl:13])[N:3]=1.FC(F)(F)C1C(C(O)=O)=NC=CC=1.CCN=C=NCCCN(C)C.Cl.C1C=C2N=NN(O)C2=CC=1.O.[Cl:50][C:51]1[C:56]([C:57](O)=[O:58])=[CH:55][CH:54]=[CH:53][N:52]=1>ClCCl.O.C(N(CC)CC)C>[Cl:50][C:51]1[N:52]=[CH:53][CH:54]=[CH:55][C:56]=1[C:57]([NH:12][CH2:11][C:8]1([C:7]2[C:2]([Cl:1])=[N:3][C:4]([Cl:13])=[CH:5][CH:6]=2)[CH2:9][CH2:10]1)=[O:58]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 762582-Chloronicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 132338443-(Trifluoromethyl)pyridine-2-carboxylic acidHCID 89544422[1-(2,6-Dichloropyridin-3-yl)cyclopropyl]methanamine

Produkt 1

HCID 71558841
2-Chloro-N-[1-(2,6-dichloro-pyridin-3-yl)-cyclopropylmethyl]nicotinamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

0.45 ml of C-[1-(2,6-dichloro-pyridin-3-yl)-cyclopropyl]-methylamine was dissolved in 1.5 ml of dichloromethane under argon and 0.11 ml of triethylamine was added at ambient temperature. Ther reaction mixture was cooled at 0° C. and 383 mg of 3-(trifluoromethyl)pyridine-2-carboxylic acid, 145 mg of EDCI.HCl, 103 mg of HOBT hydrate and 59 mg of 2-chloropyridine-3-carboxylic acid were added sequentially. The reaction mixture was stirred at ambient temperature for 14 hours. Then water was added, the phases were separated and the aqueous phase was extracted with dichloromethane. The organic layers were combined, dried with anhydrous sodium sulphate, filtered and concentrated. Crude material was obtained as a yellow sticky solid, which was purified by trituration in diethyl ether to give 60 mg of the desired 2-Chloro-N-[1-(2,6-dichloro-pyridin-3-yl)-cyclopropylmethyl]nicotinamide as white solid. 1H-NMR (CDCl3): 8.45 ppm (m, 1H), 8.04 ppm (m, 1H), 7.68 ppm (d, 1H), 7.34 ppm (m, 1H), 6.53 ppm (m, 1H), 3.72 ppm (d, 2H), 1.19 ppm (m, 2H), 0.96 ppm (m, 2H).

Aufarbeitung

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. dry with materialdried with anhydrous sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customCrude material was obtained as a yellow sticky solid, which
  7. customwas purified by trituration in diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-7b8187907c6e474389e188ea231719e9
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09040708B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion