(2,6-Dimethoxypyridin-3-yl)boronic acid → 4-amino-N-cyclopropyl-7-fluoro-8-(2,6-dimethoxypyridin-3-yl)cinnoline-3-carboxamide

HRID 2375709Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2375709
[NH2:1][C:2]1[C:11]2[C:6](=[C:7](I)[C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:14]([NH:16][CH:17]1[CH2:19][CH2:18]1)=[O:15].[CH3:20][O:21][C:22]1[C:27](B(O)O)=[CH:26][CH:25]=[C:24]([O:31][CH3:32])[N:23]=1>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:27]3[C:22]([O:21][CH3:20])=[N:23][C:24]([O:31][CH3:32])=[CH:25][CH:26]=3)[C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:14]([NH:16][CH:17]1[CH2:19][CH2:18]1)=[O:15]

Komponenten

3

Edukt 2

HCID 2762707(2,6-Dimethoxypyridin-3-yl)boronic acidHCID 672285864-amino-7-fluoro-8-iodo-N-cyclopropyl-cinnoline-3-carboxamide

Produkt 1

HCID 251832714-amino-N-cyclopropyl-7-fluoro-8-(2,6-dimethoxypyridin-3-yl)cinnoline-3-carboxamideAusbeute 67,4 %

Versuchsvorschrift

Using Method A, 4-amino-7-fluoro-8-iodo-N-cyclopropyl-cinnoline-3-carboxamide (178 mg, 0.48 mmol) and 2,6-dimethoxypyridine-3-boronic acid (176 mg, 0.96 mmol) were reacted. After purification the title compound (124 mg, 67% yield) was obtained as a white solid. 1H NMR (500 MHz, DMSO-d6) δ 9.02 (d, J=4.8 Hz, 1H), 8.51 (m, 1H), 7.73 (t, J=9.1 Hz, 1H), 7.66 (d, J=8.0 Hz, 1H), 6.51 (d, J=8.0 Hz, 1H), 3.94 (s, 3H), 3.78 (s, 3H), 2.93 (m, 1H), 0.70(m, 4H). MS APCI, m/z=384.

Aufarbeitung

  1. customwere reacted

Quellen und Nachweise

ORD-Eintrag
ord-3ce63efc55bd40e180b06d3487445eb3
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07465795B2

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