2-Chloro-3-pyridinol → 2-Chloro-3-(1-Boc-2-(R)-azetidinylmethoxy)pyridine

HRID 367078

Reaktionsgleichung

Reaktionsgleichung von HRID 367078
N[C:2]1[CH:3]=[N:4][CH:5]=[C:6](OCC2C=CC=CC=2)[CH:7]=1.C([C@@H]1CCN1CO)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=O.[Cl:29][C:30]1[C:35]([OH:36])=[CH:34][CH:33]=[CH:32][N:31]=1.FC1C=NC=C([OH:44])C=1>>[Cl:29][C:30]1[C:35]([O:36][CH2:6][C@H:7]2[CH2:2][CH2:3][N:4]2[C:5]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:44])=[CH:34][CH:33]=[CH:32][N:31]=1

Komponenten

5

Edukt 4

HCID 811362-Chloro-3-pyridinolHCID 27629063-Fluoro-5-hydroxypyridineHCID 21345256Boc-(S)-hydroxymethylazetidineHCID 229897355-(Benzyloxy)pyridin-3-amine

Produkt 1

HCID 213451652-Chloro-3-(1-Boc-2-(R)-azetidinylmethoxy)pyridine

Versuchsvorschrift

The procedures of examples 10c and 10d were used, substituting Boc-(R)-hydroxymethylazetidine for the Boc-(S)-hydroxymethylazetidine used in step 10c, and 2-chloro-3-hydroxypyridine for 3-fluoro-5-hydroxypyridine in step 10d. The title compound was obtained as an oil (535 mg, 93%): 1H NMR (CDCl3, 300 MHz) δ 1.40 (s, 9H), 2.40 (m, 2H), 3.90-4.00(m, 2H), 4.16 (m, 1H), 4.55 (m, 2H), 7.20 (m, 1H), 7.35 (m, 1H), 8.00 (m, 1H); MS (CI/NH3) m/z: 299 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-f9bf6ca87fad4facbabd372faca4a9af
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06133253

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