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

2-(Dimethylamino)acetohydrazide → HCID 178483332, Verbindung

HRID 1273020
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1273020
O1C2C=CC=CC=2C=C1[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]#[N:20])[CH:17]=2)[N:12]([CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[N:11]=1.[NH2:27][NH:28][C:29](=O)[CH2:30][N:31]([CH3:33])[CH3:32].[CH3:35][O-:36].[Na+]>CO.ClCCl>[O:36]1[C:15]2[CH:14]=[CH:13][CH:18]=[CH:17][C:16]=2[CH:19]=[C:35]1[CH:26]1[CH2:25][CH2:24][CH2:23][O:22][CH:21]1[N:12]1[C:13]2[C:18](=[CH:17][C:16]([C:19]3[NH:27][N:28]=[C:29]([CH2:30][N:31]([CH3:33])[CH3:32])[N:20]=3)=[CH:15][CH:14]=2)[CH:10]=[N:11]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 683192-(Dimethylamino)acetohydrazide2×HCID 10942334Sodium MethoxideHCID 224798583-benzo[b]furan-2-yl-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile

Produkt 1

HCID 178483332HCID 178483332, VerbindungAusbeute 7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887Methanol
Lösungsmittel
3×
HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a suspension of 3-benzo[d]furan-2-yl-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile (167 mg, 0.49 mmol) and N-amino-2-(dimethylamino)acetamide (171 mg, 1.46 mmol) in anhydrous methanol (1.0 mL) in a screw-top pressure tube was added sodium methoxide (445 μL of a 25% w/w in methanol). The tube was sealed and heated in a 100° C. oil bath for 21 h. An additional amount of N-amino-2-(dimethylamino)acetamide (171 mg, 1.46 mmol) was added and the reaction heated for an additional 2 days. The reaction was cooled, evaporated to dryness and partitioned between ethyl acetate and satd. ammonium chloride. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo to give a yellow solid. Purification of the residue by flash chromatography on silica gel using 5% methanol in dichloromethane then 20% methanol in dichloromethane gave the desired product (15 mg, 7% yield) as a pale yellow foam. ES-MS (m/z) 443 [M+H]+.

Aufarbeitung

  1. customThe tube was sealed
  2. temperaturethe reaction heated for an additional 2 days
  3. temperatureThe reaction was cooled
  4. customevaporated to dryness
  5. custompartitioned between ethyl acetate and satd
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customto give a yellow solid
  11. customPurification of the residue by flash chromatography on silica gel using 5% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-43d308c361124e3089d5bdfd9d64dfbd
Quelldatensatz
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07208513B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion