(5-Fluoro-6-methoxypyridin-3-yl)boronic acid → 4-amino-N-cyclopropyl-8-(5-fluoro-6-methoxypyridin-3-yl)cinnoline-3-carboxamide

HRID 2375718Notes

Reaction equation

HRID 2375718 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[CH:21]=[C:22](B(O)O)[CH:23]=[N:24][C:25]=1[O:26][CH3:27]>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:22]3[CH:23]=[N:24][C:25]([O:26][CH3:27])=[C:20]([F:19])[CH:21]=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 44717400(5-Fluoro-6-methoxypyridin-3-yl)boronic acidHCID 672292774-amino-8-bromo-N-cyclopropylcinnoline-3-carboxamide

Product 1

HCID 597915704-amino-N-cyclopropyl-8-(5-fluoro-6-methoxypyridin-3-yl)cinnoline-3-carboxamideYield 88%

Procedure

Using Method A, 4-amino-8-bromo-N-cyclopropyl-cinnoline-3-carboxamide (143 mg, 0.47 mmol) and 5-fluoro-6-methoxypyridine-3-boronic acid (159 mg, 0.94 mmol) were reacted. After purification the title compound (146 mg, 88% yield) was obtained as a white solid. 1H NMR (500 MHz, DMSO-d6) δ 9.13(d, J=4.9 Hz, 1H), 8.45 (d, J=7.4 Hz, 1H), 8.29 (s, 1H), 8.11 (a d, J=13.8 Hz, 1H), 7.95(a d, J=7.2 Hz, 1H), 7.81 (a t, J=7.8 Hz, 1H), 4.03 (s, 3H), 2.95 (m, 1H), 0.67 (m, 4H). MS APCI, m/z=354.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-39ad941e28d04343bd0e02913f17e41f
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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