2-Fluoro-6-methylpyridine-3-boronic acid → 4-amino-N-cyclopropyl-8-(2-fluoro-6-methylpyridin-3-yl)cinnoline-3-carboxamide

HRID 2375704Notes

Reaction equation

HRID 2375704 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7](Br)[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH:16]1[CH2:18][CH2:17]1)=[O:14].[F:19][C:20]1[C:25](B(O)O)=[CH:24][CH:23]=[C:22]([CH3:29])[N:21]=1>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:25]3[C:20]([F:19])=[N:21][C:22]([CH3:29])=[CH:23][CH:24]=3)[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH:16]1[CH2:18][CH2:17]1)=[O:14]

Participants

3

Reactant 2

HCID 27631322-Fluoro-6-methylpyridine-3-boronic acidHCID 672292774-amino-8-bromo-N-cyclopropylcinnoline-3-carboxamide

Product 1

HCID 236298554-amino-N-cyclopropyl-8-(2-fluoro-6-methylpyridin-3-yl)cinnoline-3-carboxamideYield 60.8%

Procedure

Using Method A, 4-amino-8-bromo-N-cyclopropyl-cinnoline-3-carboxamide (61 mg, 0.20 mmol) and 2-fluoro-6-methylpyridine-3-boronic acid (62 mg, 0.36 mmol) were reacted. After purification the title compound (41 mg, 60% yield) was obtained as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.52 (bm, 1H), 7.92 (a t, J=7.5 Hz, 2H), 7.85 (m, 1H), 7.75 (a t, J=7.7 Hz, 1H), 7.18 (a d, J=7.5 Hz, 1H), 2.96 (m, 1H), 2.58 (s, 3H), 0.88 (m, 2H), 0.65 (m, 2H). MS APCI, m/z=338, HPLC 2.17 min.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-e7d848d12ab74e35a322cef0532e6c16
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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