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

Hydrochloric Acid → 2-[1-(2,1,3-Benzoxadiazol-5-ylmethyl)-6-methyl-7-oxo-4-(p-tolyl)pyrrolo[2,3-c]pyridin-5-yl]-2-tert-butoxy-acetic acid

HRID 1473211
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1473211
[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([CH2:10][N:11]3[C:15]4[C:16](=[O:38])[N:17]([CH3:37])[C:18]([CH:27]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[C:28]([O:30]C)=[O:29])=[C:19]([C:20]5[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=5)[C:14]=4[CH:13]=[CH:12]3)[CH:7]=[CH:6][C:5]=12.[Li+].[OH-].Cl>O1CCCC1.CO>[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([CH2:10][N:11]3[C:15]4[C:16](=[O:38])[N:17]([CH3:37])[C:18]([CH:27]([O:32][C:33]([CH3:34])([CH3:36])[CH3:35])[C:28]([OH:30])=[O:29])=[C:19]([C:20]5[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=5)[C:14]=4[CH:13]=[CH:12]3)[CH:7]=[CH:6][C:5]=12
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 89473336methyl 2-(1-(benzo[c][1,2,5]oxadiazol-5-ylmethyl)-6-methyl-7-oxo-4-(p-tolyl)-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-(tert-butoxy)acetate

Produkt 1

HCID 715387522-[1-(2,1,3-Benzoxadiazol-5-ylmethyl)-6-methyl-7-oxo-4-(p-tolyl)pyrrolo[2,3-c]pyridin-5-yl]-2-tert-butoxy-acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887
Methanol
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of the crude methyl 2-(1-(benzo[c][1,2,5]oxadiazol-5-ylmethyl)-6-methyl-7-oxo-4-(p-tolyl)-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-(tert-butoxy)acetate in Tetrahydrofuran (THF) (1 mL) and Methanol (1 mL) was treated with 2M LiOH (1 mL, 2.000 mmol) and then heated to 70° C. for one hour. The mixture was cooled to 0° C., adjusted to pH <2 with 1N HCl and then extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by reverse phase chromatography (10-90% MeCN/H2O-0.1% TFA, 12 min.) to give the title compound. 1H NMR (400 MHz, CHLOROFORM-d) ppm 7.77-7.85 (m, 1H) 7.52-7.59 (m, 1H) 7.41-7.49 (m, 2H) 7.36-7.41 (m, 1H) 7.29-7.34 (m, 2H) 7.05-7.13 (m, 1H) 6.09-6.19 (m, 1H) 5.87-6.02 (m, 2H) 5.46-5.52 (m, 1H) 3.66 (s, 3H) 2.45 (s, 3H) 1.00 (s, 9H); LCMS (m/z) ES+=501 (M+1).

Aufarbeitung

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by reverse phase chromatography (10-90% MeCN/H2O-0.1% TFA, 12 min.)

Quellen und Nachweise

ORD-Eintrag
ord-b6a0ca1962a04bcf941dfac2632ec0f7
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09012642B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion