HCID 68182595, Verbindung → HCID 178522357, Verbindung

HRID 1623935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1623935
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:16]2[C@@H:15]3[CH2:17][C@@H:14]3[CH2:13][C:12]=2[C:11]([C:18](O)=[O:19])=[N:10]1.[NH2:21][C:22]1[CH:27]=[C:26]([OH:28])[CH:25]=[CH:24][N:23]=1>>[OH:28][C:26]1[CH:25]=[CH:24][N:23]=[C:22]([NH:21][C:18]([C:11]2[C:12]3[CH2:13][C@H:14]4[CH2:17][C@H:15]4[C:16]=3[N:9]([C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[F:1])[N:10]=2)=[O:19])[CH:27]=1

Komponenten

3

Edukt 2

HCID 68182595HCID 68182595, VerbindungHCID 178507942HCID 178507942, Verbindung

Produkt 1

HCID 178522357HCID 178522357, Verbindung

Versuchsvorschrift

A solution of 4-methoxypyridin-2-amine (100 mg, 0.806 mmol) in DCM (1.6 mL) under N2 atmosphere was cooled in an dry ice/IPA bath, and tribromoborane (0.305 mL, 3.23 mmol) was added with a syringe. After removing the cold bath, the reaction was stirred overnight at room temperature. The reaction mixture was diluted with water (5 mL) and stirred for an additional 30 min. It was then washed with saturated NaHCO3 (20 mL) to pH=7 and extracted with DCM (3×20 mL). The combined organic layer was dried over MgSO4 and concentrated to provide 2-aminopyridin-4-ol. The title compound was prepared in a manner similar to that described in Method EE using Intermediate 1 (see Example 1.1) and 2-aminopyridin-4-ol. LCMS m/z=369.3 [M+H]+; 1H NMR: (400 MHz, CD3CN) δ ppm 0.50 (td, J=4.7 and 3.5 Hz, 1H), 1.22 (td, J=7.8 and 4.9 Hz, 1H), 2.21-2.26 (m, 1H), 2.31-2.38 (m, 1H), 2.93 (d, J=16.7 Hz, 1H), 3.05 (dd, J=16.6 and 6.3 Hz, 1H), 6.80 (dd, J=7.1 and 2.2 Hz, 1H), 6.95 (d, J=2.2 Hz, 1H), 7.15-7.21 (m, 1H), 7.22-7.29 (m, 1H), 7.52 (s, 1H), 7.70 (td, J=8.8 and 5.9 Hz, 1H), 7.82 (d, J=7.1 Hz, 1H).

Quellen und Nachweise

ORD-Eintrag
ord-7bda950a0a6b44d58bd7862c79f6905a
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778950B2

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