Monoethyl malonate → ethyl 3-(4-(5-(5-amino-6-(5-(tert-butyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)-1-ethyl-1H-1,2,4-triazol-3-yl)piperidin-1-yl)-3-oxopropanoate

HRID 1749692Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1749692
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[CH2:25]([O:27][C:28](=[O:33])[CH2:29][C:30]([OH:32])=O)[CH3:26].C(N(C(C)C)C(C)C)C.[C:43]([C:47]1[O:51][C:50]([C:52]2[C:53]([NH2:71])=[N:54][CH:55]=[C:56]([C:58]3[N:62]([CH2:63][CH3:64])[N:61]=[C:60]([CH:65]4[CH2:70][CH2:69][NH:68][CH2:67][CH2:66]4)[N:59]=3)[N:57]=2)=[N:49][N:48]=1)([CH3:46])([CH3:45])[CH3:44]>CN(C=O)C>[NH2:71][C:53]1[N:54]=[CH:55][C:56]([C:58]2[N:62]([CH2:63][CH3:64])[N:61]=[C:60]([CH:65]3[CH2:66][CH2:67][N:68]([C:30](=[O:32])[CH2:29][C:28]([O:27][CH2:25][CH3:26])=[O:33])[CH2:69][CH2:70]3)[N:59]=2)=[N:57][C:52]=1[C:50]1[O:51][C:47]([C:43]([CH3:44])([CH3:45])[CH3:46])=[N:48][N:49]=1

Komponenten

6

Edukt 4

HCID 70615Monoethyl malonateHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86727668HCID 86727668, Verbindung

Produkt 1

HCID 86727674ethyl 3-(4-(5-(5-amino-6-(5-(tert-butyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)-1-ethyl-1H-1,2,4-triazol-3-yl)piperidin-1-yl)-3-oxopropanoateAusbeute 147 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (474 mg, 1.25 mmol) was added over 30 seconds in portions to a stirred solution of 3-ethoxy-3-oxopropanoic acid (150 mg, 1.13 mmol), N-ethyl-N-isopropylpropan-2-amine (0.394 mL, 2.26 mmol) and 3-(5-(tert-butyl)-1,3,4-oxadiazol-2-yl)-5-(1-ethyl-3-(piperidin-4-yl)-1H-1,2,4-triazol-5-yl)pyrazin-2-amine (450 mg, 1.13 mmol) dissolved in DMF (20 mL) at 50° C. The resulting solution was sampled after 1 min (complete reaction) and immediately allowed to cool to ambient temperature. The reaction mixture was concentrated and diluted with EtOAc (100 mL), and washed sequentially with water (20 mL) and saturated brine (20 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude ethyl 3-(4-(5-(5-amino-6-(5-(tert-butyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)-1-ethyl-1H-1,2,4-triazol-3-yl)piperidin-1-yl)-3-oxopropanoate (850 mg).

Aufarbeitung

  1. aliquotThe resulting solution was sampled after 1 min
  2. custom(complete reaction)
  3. concentrationThe reaction mixture was concentrated
  4. additiondiluted with EtOAc (100 mL)
  5. washwashed sequentially with water (20 mL) and saturated brine (20 mL)
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-354c2ad5811c42dfb1c214f525958c64
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156831B2

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