Ammonium Acetate → HCID 178480123, Verbindung

HRID 592059Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 592059
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([NH:9][C@@H:10]2[C@@H:15]3[O:16][C@@H:12]([CH2:13][CH2:14]3)[C@@H:11]2[C:17]([NH2:19])=[O:18])[C:5]([Cl:20])=[CH:4][N:3]=1.[CH3:21][N:22]1[CH:26]=[C:25]([CH:27]=O)[CH:24]=[N:23]1.C([O-])(=O)C.[NH4+]>CCO>[Cl:20][C:5]1[C:6]([NH:9][C@@H:10]2[C@@H:15]3[O:16][C@@H:12]([CH2:13][CH2:14]3)[C@@H:11]2[C:17]([NH2:19])=[O:18])=[C:7]2[N:8]=[C:27]([C:25]3[CH:24]=[N:23][N:22]([CH3:21])[CH:26]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 517165Ammonium AcetateHCID 5731171-Methyl-1H-pyrazole-4-carbaldehydeHCID 89738581HCID 89738581, Verbindung

Produkt 1

HCID 178480123HCID 178480123, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

(1S,2R,3S,4R)-3-(2,3-diamino-5-chloropyridin-4-ylamino)-7-oxabicyclo[2.2.1]heptane-2-carboxamide (17) (90 mg, 0.302 mmol), 1-methyl-1H-pyrazole-4-carbaldehyde (30 mg, 0.272 mmol) were taken in EtOH (15 ml) to which ammonium acetate (35 mg) was added and the reaction mixture was heated at 70° C. for 48 h. Crude LCMS showed the desired product along with trace of starting material. The reaction mixture was allowed to come to rt and the precipitated was filtered and washed well with hot ethanol to afford the desired product (70 mg, 41%) as a white solid. NMR: δ (1H, 400M Hz, DMSO-d6): 1.40-1.80 (4H, m), 2.92 (1H, d, J=8.4 Hz), 3.92 (3H, s), 4.28 (1H, s), 4.56 (1H, s), 5.40-5.55 (1H, m), 6.82 (1H, s), 7.14 (1H, s), 7.1 (1H, s), 7.86 (1H, s), 7.99 (1H, s), 8.23 (1H, s).

Aufarbeitung

  1. additionwas added

Quellen und Nachweise

ORD-Eintrag
ord-c3d8b55d767c401b863c56839877a04f
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238656B2

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