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

Diisopropylethylamine → 7-(2-Amino-4-methyl-1H-benzo[d]imidazol-6-yl)-1-((tetrahydro-2H-pyran-4-yl)Methyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one

HRID 1525476
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1525476
Br[C:2]1[N:3]=[C:4]([NH:15][CH2:16][CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:5]([NH:8][CH2:9][C:10]([O:12]CC)=O)=[N:6][CH:7]=1.BrC1[C:25]([NH:31]CC(OCC)=O)=[N:26][CH:27]=[C:28](Br)N=1.O1[CH2:43][CH2:42][CH:41]([CH2:44][NH2:45])[CH2:40]C1.C(N(CC)C(C)C)(C)C>CO.CS(C)=O>[NH2:31][C:25]1[NH:26][C:27]2[CH:28]=[C:43]([C:2]3[N:3]=[C:4]4[N:15]([CH2:16][CH:17]5[CH2:18][CH2:19][O:20][CH2:21][CH2:22]5)[C:10](=[O:12])[CH2:9][NH:8][C:5]4=[N:6][CH:7]=3)[CH:42]=[C:41]([CH3:40])[C:44]=2[N:45]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 27732104-AminomethyltetrahydropyranHCID 57550751Ethyl 2-(3,5-dibromopyrazin-2-ylamino)acetateHCID 86644641Ethyl 2-(5-bromo-3-((tetrahydro-2H-pyran-4-yl)methylamino)pyrazin-2-ylamino)acetate

Produkt 1

HCID 582983117-(2-Amino-4-methyl-1H-benzo[d]imidazol-6-yl)-1-((tetrahydro-2H-pyran-4-yl)Methyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

Ethyl 2-(5-bromo-3-((tetrahydro-2H-pyran-4-yl)methylamino)pyrazin-2-ylamino)acetate. Ethyl 2-(3,5-dibromopyrazin-2-ylamino)acetate (2.00 g, 5.90 mmol), (tetrahydro-2H-pyran-4-yl)methanamine (0.713 g, 6.19 mmol), N,N-diisopropylethylamine (3.08 mL, 17.70 mmol) and dimethylsulfoxide (4 mL) were combined in a microwave vial with a stirbar and heated in a Biotage Emrys Optimizer microwave reactor at 150° C. for 1 h. The resulting mixture was transferred to a round bottom flask with methanol. The methanol and N,N-diisopropylethylamine were removed under reduced pressure and the residue purified using Biotage flash chromatography (5-100% ethyl acetate in hexane). Fractions containing the desired product were combined in a reparatory funnel and washed twice with water and once with brine. The organics were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was dried under high vacuum at 50° C. to give impure desired product (1.578 g) as an amber waxy solid which was taken on to the next step without further purification. MS (ESI) m/z 373.4 [M]+, 375.4 [M+2]+.

Aufarbeitung

  1. customThe methanol and N,N-diisopropylethylamine were removed under reduced pressure
  2. customthe residue purified
  3. additionFractions containing the desired product
  4. customwere combined in a reparatory funnel
  5. washwashed twice with water and once with brine
  6. dry with materialThe organics were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was dried under high vacuum at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-6e53d9a4fa1f4284a2107608e49ff657
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09079900B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion