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

HRID 2375699Notes

Reaction equation

HRID 2375699 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7](Br)[C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:14]([NH:16][CH:17]1[CH2:20][CH2:19][CH2:18]1)=[O:15].[CH3:21][O:22][C:23]1[C:28](B(O)O)=[CH:27][CH:26]=[C:25]([O:32][CH3:33])[N:24]=1>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:28]3[C:23]([O:22][CH3:21])=[N:24][C:25]([O:32][CH3:33])=[CH:26][CH:27]=3)[C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:14]([NH:16][CH:17]1[CH2:20][CH2:19][CH2:18]1)=[O:15]

Participants

3

Reactant 2

HCID 2762707(2,6-Dimethoxypyridin-3-yl)boronic acidHCID 67229734HCID 67229734, compound

Product 1

HCID 251835544-amino-N-cyclobutyl-8-(2,6-dimethoxypyridin-3-yl)-7-fluoro-cinnoline-3-carboxamideYield 59.5%

Procedure

Using Method A, 4-amino-8-bromo-7-fluoro-N-cyclobutyl-cinnoline-3-carboxamide (175 mg) and 2,6-dimethoxypyridin-3-yl boronic acid (206 mg) were reacted to afford the title compound (122 mg) as white solid. 1H NMR (500 MHz, DMSO-d6) δ 9.22 (d, 1H), 8.50 (m, 1H), 7.73 (t, 1H), 7.67 (d, 1H), 6.53 (d, 1H), 4.49 (m, 1H), 3.95 (s, 3H), 3.80 (s, 3H), 2.26-2.10(m, 4H), 1.72-1.62 (m, 2H). MS APCI, m/z=398 (M+H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-16a9a9cc240d4d3ba867d93daecc98b4
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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