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

Methanamine, N-methoxy-, hydrochloride (1:1) → (+/-)-tert-butyl 1-(1-(methoxy(methyl)amino)-1-oxopropan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

HRID 1527053
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1527053
CO[C:3](=[O:23])[CH:4]([N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[C:8]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[C:7]1[CH3:22])[CH3:5].Cl.[CH3:25][NH:26][O:27][CH3:28].C([Mg]Cl)(C)C>>[CH3:28][O:27][N:26]([CH3:25])[C:3](=[O:23])[CH:4]([N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[C:8]([C:15]([O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:16])=[C:7]1[CH3:22])[CH3:5]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 117779095(+/-)-tert-butyl 1-(1-methoxy-1-oxopropan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylateHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 117779094(+/-)-tert-butyl 1-(1-(methoxy(methyl)amino)-1-oxopropan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylateAusbeute 60,3 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a 100 mL round-bottom flask was added (±)-tert-butyl 1-(1-methoxy-1-oxopropan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate (0.958 g, 3.01 mmol) and N,O-dimethylhydroxylamine hydrochloride (0.440 g, 4.51 mmol). The flask was vac/purged 3× with N2 then THF (17 mL) were added and the reaction was cooled to −40° C. isopropylmagnesium chloride (4.51 ml, 9.03 mmol) was added dropwise and the reaction was mixed at that temperature for 1 h then warmed to 0° C. for 1 h then quenched with 1N HCl, extracted with EtOAc. The org layer was washed with water then brine, dried over Na2SO4, filtered, concentrated, deposited onto silica gel with aid of DCM, and purified by CC using 25% EtOAc in Hex as eluent to provide (±)-tert-butyl 1-(1-(methoxy(methyl)amino)-1-oxopropan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate (0.630 g, 60.3%). LRMS (M+H+) m/z: calcd 348.41. found 348.2.

Aufarbeitung

  1. customThe flask was vac/purged 3× with N2
  2. additionTHF (17 mL) were added
  3. additionwas added dropwise
  4. additionthe reaction was mixed at that temperature for 1 h
  5. customthen quenched with 1N HCl
  6. extractionextracted with EtOAc
  7. washThe org layer was washed with water
  8. dry with materialbrine, dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. custompurified by CC

Quellen und Nachweise

ORD-Eintrag
ord-bc8034db89f0467c88359c4203c76243
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09085583B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion