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

Trifluoroacetic acid → 6-(2-chloro-4-(1,3,4-oxadiazol-2-yl)phenyl)-8-ethyl-2-(4-(4-methylpiperazin-1-yl)phenylamino)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 387219
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 387219
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]1[C:35](=[O:36])[N:34]([CH2:37][CH3:38])[C:15]2[N:16]=[C:17]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([N:27]4[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]4)=[CH:23][CH:22]=3)[N:18]=[CH:19][C:14]=2[CH:13]=1)[C:5]([NH:7][NH2:8])=[O:6].F[C:40](F)(F)C(O)=O>C(OCC)(OCC)OCC>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[O:6][CH:40]=[N:8][N:7]=2)[CH:9]=[CH:10][C:11]=1[C:12]1[C:35](=[O:36])[N:34]([CH2:37][CH3:38])[C:15]2[N:16]=[C:17]([NH:20][C:21]3[CH:22]=[CH:23][C:24]([N:27]4[CH2:28][CH2:29][N:30]([CH3:33])[CH2:31][CH2:32]4)=[CH:25][CH:26]=3)[N:18]=[CH:19][C:14]=2[CH:13]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 671196213-Chloro-4-{8-ethyl-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl}benzoic acid hydrazide

Produkt 1

HCID 513542406-(2-chloro-4-(1,3,4-oxadiazol-2-yl)phenyl)-8-ethyl-2-(4-(4-methylpiperazin-1-yl)phenylamino)pyrido[2,3-d]pyrimidin-7(8H)-oneAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31214
Ethyl orthoformate
Lösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

3-Chloro-4-{8-ethyl-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl}benzoic acid hydrazide (7, 30 mg, 0.06 mmol) was suspended in triethyl orthoformate (5 mL) to which was added trifluoroacetic acid (1 mL). The resulting reaction mixture was heated at 130° C. for 2 h. The volatiles were removed and the residue was taken up in dichloromethane (1×20 mL) and washed with 10% sodium hydroxide solution (2×10 mL). The organic layer was dried over sodium sulfate, filtered and evaporated. The residue was purified by column chromatography using dichloromethane:methanol (95:5). The title compound (18 mg, 0.03 mmol, 50%) was obtained as a yellow solid. ESMS m/z 543 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 8.57 (s, 1H) 8.50 (s, 1H) 8.21 (d, J=1.5 Hz, 1H) 8.04 (dd, J=8.0, 1.5 Hz, 1H) 7.62 (s, 1H) 7.52-7.60 (m, 3H) 7.29 (br. s., 1H) 6.98 (d, J=9.0 Hz, 2H) 4.50 (q, J=6.8 Hz, 2H) 3.16-3.27 (m, 4H) 2.56-2.65 (m, 4H) 2.37 (s, 3H) 1.39 (d, J=6.8 Hz, 3H).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customThe volatiles were removed
  3. washwashed with 10% sodium hydroxide solution (2×10 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f0ea3ee6287b470690f1e2aacb091cfe
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08372970B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion