Ammonium Acetate → HCID 178493034, Verbindung

HRID 592060Notizen

Reaktionsgleichung

[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][O:22][C:23]1[CH:30]=[C:29]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[CH:28]=[CH:27][C:24]=1[CH:25]=O.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:25]([C:24]3[CH:27]=[CH:28][C:29]([N:31]4[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)=[CH:30][C:23]=3[O:22][CH3:21])[NH:1][C:2]2=[N:3][CH:4]=1

Komponenten

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) (140 mg, 0.47 mmol), 2-methoxy-4-morpholinobenzaldehyde (93 mg, 0.42 mmol) were taken in EtOH (15 ml) to which ammonium acetate (40 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 (120 mg, 51%) as an off white solid. NMR: δ (1H, 400M Hz, CDCl3): 1.50-1.80 (4H, m), 2.95 (1H, d, J=8.4 Hz), 3.27 (4H, bs), 3.76 (4H, bs), 3.96 (3H, s), 4.32 (1H, d, J=4.4 Hz), 4.57 (1H, s), 5.51 (1H, t, J=4.4 Hz), 6.63 (1H, s), 6.69 (1H, d, J=8.4 Hz), 6.90 (1H, d, J=8.4 Hz), 7.18 (1H, s), 7.60 (1H, s), 7.91 (1H, s), 8.05 (1H, d, J=8.8 Hz), 12.14 (1H, s). LCMS (254 nm): [M+H]+ 499.00 (100%). HPLC: (254 nm) 97.68%.

Aufarbeitung

additionwas added

Quellen und Nachweise

ORD-Eintrag: ord-cee6396f7451424a9a862d648b843659
Quelldatensatz: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09238656B2

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