Dimethylformamide → (S)-1-(4-chlorophenyl)-N-(1-(pyrrolo[1,2-a]pyrazin-1-yl)pyrrolidin-3-yl)-1H-1,2,4-triazole-3-carboxamide

HRID 1755272Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1755272
C1(C2O[N:10]=[C:9]([C:12]([OH:14])=O)[N:8]=2)C=CC=CC=1.[ClH:15].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.C(N(CC)[CH:34]([CH3:36])[CH3:35])C.CN(C(ON1N=N[C:49]2[CH:50]=[CH:51][CH:52]=N[C:48]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C[N:64]([CH:66]=O)[CH3:65]>C(OCC)(=O)C>[Cl:15][C:50]1[CH:51]=[CH:52][C:65]([N:64]2[CH:66]=[N:8][C:9]([C:12]([NH:30][C@H:27]3[CH2:28][CH2:29][N:25]([C:24]4[C:23]5[N:22]([CH:36]=[CH:34][CH:35]=5)[CH:21]=[CH:20][N:19]=4)[CH2:26]3)=[O:14])=[N:10]2)=[CH:48][CH:49]=1

Komponenten

7

Edukt 5

HCID 6228DimethylformamideHCID 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 75202693(S)-1-(4-chlorophenyl)-N-(1-(pyrrolo[1,2-a]pyrazin-1-yl)pyrrolidin-3-yl)-1H-1,2,4-triazole-3-carboxamideAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 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 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 purified by reverse phase HPLC (acetonitrile-H2O with 0.1% TFA as eluent) to give 26 mg of the title compound (23% yield) as white solid.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-4b6c9babee384915b712dd58e86abc2a
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09169261B2

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