Acetyl chloride → 1-[3-(2-{[(1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl]methoxy}-1,5-naphthyridin-3-yl)piperidin-1-yl]ethanone

HRID 872066Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 872066
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[CH2:11][C@@H:10]2[CH2:12][O:13][C:14]2[C:23]([CH:24]3[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]3)=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][N:20]=3)[N:15]=2)=[N:7][CH:8]=1.[C:30](Cl)(=[O:32])[CH3:31].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[CH2:11][C@@H:10]2[CH2:12][O:13][C:14]2[C:23]([CH:24]3[CH2:29][CH2:28][CH2:27][N:26]([C:30](=[O:32])[CH3:31])[CH2:25]3)=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][N:20]=3)[N:15]=2)=[N:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 1176891582-{[(1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl]methoxy}-3-(piperidin-3-yl)-1,5-naphthyridine

Produkt 1

HCID 710858851-[3-(2-{[(1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl]methoxy}-1,5-naphthyridin-3-yl)piperidin-1-yl]ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-{[(1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl]methoxy}-3-(piperidin-3-yl)-1,5-naphthyridine (RR3) (12 mg, 0.03 mmol) in DMF (0.3 mL) was added acetyl chloride (0.006 mL, 0.09 mmol) and Hunig's Base (0.015 mL, 0.09 mmol). After five minutes, the mixture was purified directly by reverse phase chromatography (Waters Sunfire Prep C18 OBD, 5-60% acetonitrile in water with 0.1% TFA modifier) to afford the title compound. 1H NMR (500 MHz, DMSO): δ 8.78 (s, 1 H), 8.13 (s, 3 H), 7.64 (s, 1 H), 7.26 (m, 2 H), 4.50 (m, 2 H), 4.26 (brs, 2 H), 3.77 (s, 3 H), 3.49-3.40 (m, 2 H), 3.08 (m, 2 H), 2.27 (m, 2 H), 2.24-2.19 (m, 1 H), 2.05 (s, 3 H), 1.80 (s, 1 H), 1.23-1.15 (m, 2 H), 1.08 (dt, J=8.7, 4.6 Hz, 1 H); HRMS m/z (M+H) 433.2228 found, 433.2234 required.

Aufarbeitung

  1. customthe mixture was purified directly by reverse phase chromatography (Waters Sunfire Prep C18 OBD, 5-60% acetonitrile in water with 0.1% TFA modifier)

Quellen und Nachweise

ORD-Eintrag
ord-1c31c67c57b94f77bbd30c8a845978dc
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975261B2

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