N,N-Diethyl-2-propanamine → (S)-N-(1-(imidazo[1,2-a]pyrazin-8-yl)pyrrolidin-3-yl)-5-phenyl-1,2,4-oxadiazole-3-carboxamide

HRID 1755271Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1755271
[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]([OH:14])=O)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.N1C=N[N:19]2[C:24]([N:25]3[CH2:29][CH2:28][C@H:27]([NH2:30])[CH2:26]3)=[CH:23][N:22]=[CH:21][C:20]=12.[CH2:31]([N:33](CC)C(C)C)[CH3:32].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[N:33]1[CH:31]=[CH:32][N:22]2[CH:21]=[CH:20][N:19]=[C:24]([N:25]3[CH2:29][CH2:28][C@H:27]([NH:30][C:12]([C:9]4[N:8]=[C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[O:11][N:10]=4)=[O:14])[CH2:26]3)[C:23]=12

Komponenten

7

Edukt 4

HCID 521913N,N-Diethyl-2-propanamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 218070875-Phenyl-1,2,4-oxadiazole-3-carboxylic acidHCID 86720545(S)-1-([1,2,4]triazolo[1,5-a]pyrazin-5-yl)pyrrolidin-3-amine hydrochloride salt

Produkt 1

HCID 75202692(S)-N-(1-(imidazo[1,2-a]pyrazin-8-yl)pyrrolidin-3-yl)-5-phenyl-1,2,4-oxadiazole-3-carboxamideAusbeute 23,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of the above 5-phenyl-1,2,4-oxadiazole-3-carboxylic acid (58 mg, 0.3 mmol), (S)-1-([1,2,4]triazolo[1,5-a]pyrazin-5-yl)pyrrolidin-3-amine hydrochloride salt (90 mg, 0.32 mmol) in DMF (5 mL) was added diethylisopropyl amine (650 mg, 5 mmol), followed by HATU (120 mg, 0.31 mmol). The resulting solution was stirred at room temperature for 1 h. The reaction mixture was then diluted with ethyl acetate and washed with saturated aqueous solutions of KH2PO4 and NaHCO3, followed by brine. The organic layer was concentrated in vacuo and the residue was purified by reverse phase HPLC (acetonitrile-H2O with 0.1% TFA as eluent) to give 26 mg of the title compound (23% yield) as a white solid. MS: (ES) m/z found 376.2.

Aufarbeitung

  1. washwashed with saturated aqueous solutions of KH2PO4 and NaHCO3
  2. concentrationThe organic layer was concentrated in vacuo
  3. customthe residue was purified by reverse phase HPLC (acetonitrile-H2O with 0.1% TFA as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-70dd2a955ba549e7b0ee73f7559e2587
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09169261B2

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