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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 1640299
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1640299
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 separatory 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 separatory 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-1df4392fe91f43b59882fba4de7ca668
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08110578B2

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