Methanedione--ethanol (1/1) → (S)-N-(4-(Chlorodifluoromethoxy)phenyl)-6-((3,4-dihydroxybutyl)amino)-5-(1H-pyrazol-5-yl)nicotinamide

HRID 525781

Reaktionsgleichung

Reaktionsgleichung von HRID 525781
C(=O)=O.CCO.[Cl:7][C:8]([F:38])([F:37])[O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:36])[C:18]2[CH:23]=[C:22]([C:24]3[NH:28][N:27]=[CH:26][CH:25]=3)[C:21]([NH:29][CH2:30][CH2:31][CH:32]([OH:35])[CH2:33][OH:34])=[N:20][CH:19]=2)=[CH:12][CH:11]=1>>[Cl:7][C:8]([F:37])([F:38])[O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:36])[C:18]2[CH:23]=[C:22]([C:24]3[NH:28][N:27]=[CH:26][CH:25]=3)[C:21]([NH:29][CH2:30][CH2:31][C@H:32]([OH:35])[CH2:33][OH:34])=[N:20][CH:19]=2)=[CH:12][CH:11]=1

Komponenten

3

Edukt 2

HCID 19604758Methanedione--ethanol (1/1)HCID 89907837N-(4-(Chlorodifluoromethoxy)phenyl)-6-((3,4-dihydroxybutyl)amino)-5-(1H-pyrazol-5-yl)nicotinamide

Produkt 1

HCID 118044945(S)-N-(4-(Chlorodifluoromethoxy)phenyl)-6-((3,4-dihydroxybutyl)amino)-5-(1H-pyrazol-5-yl)nicotinamide

Versuchsvorschrift

The title compound was prepared by chiral separation (Preparative chiral SFC, ChiralPak® AD-H, 250×30 mm, mobile phase: CO2/EtOH (3:2), flow rate: 50 mL/min, back pressure: 100 bar, column temperature: 38° C., wavelength: 220 nm, cycle time: 6.0 min) of a racemic mixture of N-(4-(chlorodifluoromethoxy)phenyl)-6-((3,4-dihydroxybutyl)amino)-5-(1H-pyrazol-5-yl)nicotinamide (Example 100), faster eluting isomer (Peak 1). Or alternatively in an analogous fashion to that described in Example 97 using (S)-benzyl(3,4-dihydroxybutyl)carbamate (Stage 101.1) as chiral starting material. Analytical chiral SFC (ChiralPak® AD-H, 250×4.6 mm, 5 μm, eluent: CO2/EtOH+0.05% DEA (3:2), flow rate: 2.4 mL/min, back pressure: 100 bar, temperature: 35° C., 220 nm): tR=3.18 min.

Aufarbeitung

  1. washfaster eluting isomer (Peak 1)
  2. custom35° C., 220 nm

Quellen und Nachweise

ORD-Eintrag
ord-c85d5bc3e19440f6974c0577de276510
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340537B2

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