Acetic Acid → HCID 178442411, Verbindung

HRID 2171872

Reaktionsgleichung

Reaktionsgleichung von HRID 2171872
[OH-].[Na+].[OH:3][NH:4][C:5](N)=[O:6].Br[CH:9]([CH:14](Br)[CH2:15][CH:16]([NH:21][C:22]1[C:27]([F:28])=[CH:26][N:25]=[C:24]([C:29]2[C:37]3[C:32](=[N:33][CH:34]=[C:35]([F:38])[CH:36]=3)[NH:31][CH:30]=2)[N:23]=1)[C:17]([CH3:20])([CH3:19])[CH3:18])C(OC)=O.CC(O)=O>O.CO>[F:28][C:27]1[C:22]([NH:21][CH:16]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:15][C:14]2[O:3][N:4]=[C:5]([OH:6])[CH:9]=2)=[N:23][C:24]([C:29]2[C:37]3[C:32](=[N:33][CH:34]=[C:35]([F:38])[CH:36]=3)[NH:31][CH:30]=2)=[N:25][CH:26]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 3657HydroxyureaHCID 14798Sodium HydroxideHCID 86714756methyl 2,3-dibromo-5-((5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)amino)-6,6-dimethylheptanoate2×

Produkt 1

HCID 178442411HCID 178442411, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of NaOH (0.015 g) dissolved in water (0.410 mL) was added hydroxyurea (0.008 g, 0.100 mmol). The resulting mixture was stirred for 30 minutes before the dropwise addition of methyl 2,3-dibromo-5-((5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)amino)-6,6-dimethylheptanoate, 85a, (0.064 g, 0.110 mmol) in MeOH (0.150 mL). The solution was stirred for 6 hours before the addition of AcOH (0.031 mL). The residue was purified by reverse phase preparative HPLC to afford the desired product: 1H NMR (300 MHz, MeOD) δ 8.57 (dd, J=9.7, 2.8 Hz, 1H), 8.16 (d, J=5.5 Hz, 2H), 8.00 (d, J=4.1 Hz, 1H), 5.68 (s, 1H), 3.03 (ddd, J=27.4, 15.4, 12.3 Hz, 2H), 1.10 (d, J=3.3 Hz, 11H); LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, RT=2.15 minutes (M+H) 416.04.

Aufarbeitung

  1. customThe residue was purified by reverse phase preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-8529576a69794fbbb74459923dc1bf04
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051319B2

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