6-chloro-N-(3-fluoropyridin-4-yl)-8-(isoxazol-3-ylamino)imidazo[1,2-b]pyridazine-3-carboxamide → HCID 178522303, Verbindung

HRID 1943463

Reaktionsgleichung

Cl[C:2]1[CH:3]=[C:4]([NH:21][C:22]2[CH:26]=[CH:25][O:24][N:23]=2)[C:5]2[N:6]([C:8]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][N:17]=[CH:16][C:15]=3[F:20])=[O:12])=[CH:9][N:10]=2)[N:7]=1.[NH2:27][C@H:28]1[CH2:33][CH2:32][C@H:31]([OH:34])[CH2:30][CH2:29]1>CN1C(=O)CCC1>[F:20][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:14]=1[NH:13][C:11]([C:8]1[N:6]2[N:7]=[C:2]([NH:27][C@H:28]3[CH2:33][CH2:32][C@H:31]([OH:34])[CH2:30][CH2:29]3)[CH:3]=[C:4]([NH:21][C:22]3[CH:26]=[CH:25][O:24][N:23]=3)[C:5]2=[N:10][CH:9]=1)=[O:12]

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

A mixture of 6-chloro-N-(3-fluoropyridin-4-yl)-8-(isoxazol-3-ylamino)imidazo[1,2-b]pyridazine-3-carboxamide (20 mg, 0.054 mmol) and (trans)-4-aminocyclohexanol (61.6 mg, 0.535 mmol) in NMP (0.4 mL) was heated at 110° C. overnight. The reaction mixture was cooled to room temperature, and purified by reversed-phase preparative HPLC. The desired fractions were concentrated and dried to give 15 mg the title compound as a beige solid. HPLC Rt=2.615 min (Chromolith SpeedROD 4.6×50 mm, 10-90% aqueous methanol containing 0.1% TFA, 4 min gradient, monitored at 220 nm), [M+1]=453.

Aufarbeitung

temperatureThe reaction mixture was cooled to room temperature
custompurified by reversed-phase preparative HPLC
concentrationThe desired fractions were concentrated
customdried

Quellen und Nachweise

ORD-Eintrag: ord-be5a1e2d52d744679539ac168f213b6b
Quelldatensatz: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08389527B2

Verknüpfte Notizen

Wird geladen…