Reaktion #166513

ord-c3362d14a019415d972419ceedcbccfe

Reaktionsgleichung

CCc1nn(Cc2cccc(C)n2)c2cccc(NC(=O)c3cnc4cc(F)ccn34)c12
N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-fluoroimidazo[1,2-a]pyridine-3-carboxamide
CC(C)(C)OC(=O)N1C[C@H](O)[C@@H](O)C1
(3S,4S)-tert-butyl 3,4-dihydroxypyrrolidine-1-carboxylate
CC(C)(C)[O-].[K+]
potassium tert-butoxide
CCc1nn(Cc2cccc(C)n2)c2cccc(NC(=O)c3cnc4cc(O[C@H]5CN(C(=O)OC(C)(C)C)C[C@@H]5O)ccn34)c12
crude product
Ausbeute 91.5%
CCc1nn(Cc2cccc(C)n2)c2cccc(NC(=O)c3cnc4cc(O[C@H]5CN(C(=O)OC(C)(C)C)C[C@@H]5O)ccn34)c12
(3S,4S)-tert-butyl 3-(3-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-ylcarbamoyl)imidazo[1,2-a]pyridin-7-yloxy)-4-hydroxypyrrolidine-1-carboxylate
Ausbeute 91.5%

Lösungsmittel

Reaktionsbedingungen

Temperatur
100°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Einengenconcentrated under reduced pressure

Vorschrift

To N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-fluoroimidazo[1,2-a]pyridine-3-carboxamide (32 mg, 0.075 mmol; prepared as in Example 74, Step A) in THF/t-BuOH (1 mL/1 mL) was added (3S,4S)-tert-butyl 3,4-dihydroxypyrrolidine-1-carboxylate (61 mg, 0.30 mmol) and potassium tert-butoxide (67 mg, 0.60 mmol). The reaction was heated with microwave at 100° C. for 50 minutes, and then concentrated under reduced pressure. Silica gel chromatography (DCM/MeOH 10:1) gave the crude product (42 mg).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08841455B2uspto-grants-2014_09