Potassium Fluoride → (Rac)-{1-[3-(7-fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]-pyrrolidin-3-yl}-methyl-carbamic acid tert-butyl ester

HRID 69270

Reaktionsgleichung

Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][C:21]=3[F:22])[N:18]=[CH:17][CH:16]=[CH:15]4)=[CH:9][N:10]=2)[N:7]=1.[F-].[K+].[C:25]([O:29][C:30](=[O:38])[N:31]([CH3:37])[CH:32]1[CH2:36][CH2:35][NH:34][CH2:33]1)([CH3:28])([CH3:27])[CH3:26]>CN1C(=O)CCC1.CC(OC)(C)C>[C:25]([O:29][C:30](=[O:38])[N:31]([CH:32]1[CH2:36][CH2:35][N:34]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8]([CH2:11][C:12]4[CH:13]=[C:14]5[C:19](=[CH:20][C:21]=4[F:22])[N:18]=[CH:17][CH:16]=[CH:15]5)=[CH:9][N:10]=3)[N:7]=2)[CH2:33]1)[CH3:37])([CH3:28])([CH3:26])[CH3:27]

Komponenten

Reaktionsbedingungen

Temperatur: 170 °C

Versuchsvorschrift

6-(6-Chloro-imidazo[1,2-b]pyridazin-3-ylmethyl)-7-fluoro-quinoline (Stage 173.1, 150 mg, 0.474 mmol), KF (139 mg, 2.372 mmol) and (rac)-methyl-pyrrolidin-3-yl-carbamic acid tert-butyl ester (285 mg, 1.423 mmol) were suspended in NMP (1.5 mL). The RM was stirred at 170° C. for 1 h. The mixture was diluted with TBME and washed with water (3×). The aqueous phases were further extracted with TBME (1×). The combined organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was crystallized in Et2O to afford the title compound as a beige solid (tR 3.91 min (conditions 13), MH+=477).

Aufarbeitung

washwashed with water (3×)
extractionThe aqueous phases were further extracted with TBME (1×)
dry with materialThe combined organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was crystallized in Et2O

Quellen und Nachweise

ORD-Eintrag: ord-69c857447bb649fdbad863c547a7bccb
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08822468B2

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