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

HRID 2375679Notes

Reaction equation

HRID 2375679 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].[CH3:19][O:20][C:21]1[C:26](B(O)O)=[CH:25][CH:24]=[C:23]([O:30][CH3:31])[N:22]=1>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:26]3[C:21]([O:20][CH3:19])=[N:22][C:23]([O:30][CH3:31])=[CH:24][CH:25]=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 2762707(2,6-Dimethoxypyridin-3-yl)boronic acidHCID 672292774-amino-8-bromo-N-cyclopropylcinnoline-3-carboxamide

Product 1

HCID 236296944-amino-N-cyclopropyl-8-(2,6-dimethoxypyridin-3-yl)cinnoline-3-carboxamideYield 77%

Procedure

Using Method A, 4-amino-8-bromo-N-cyclopropyl-cinnoline-3-carboxamide (143 mg, 0.47 mmol) and 2,6-dimethoxypyridine-3-boronic acid (170 mg, 0.94 mmol) were reacted. After purification the title compound (132 mg, 77% yield) was obtained as a white solid. 1H NMR (500 MHz, DMSO-d6) δ 9.03 (d, J=4.9 Hz, 1H), 8.38 (d, J=8.0 Hz, 1H), 7.76 (m, 2H), 7.67 (d, J=8.0 Hz, 1H), 6.48 (d, J=8.0 Hz, 1H), 3.93 (s, 3H), 3.77 (s, 3H), 2.96 (m, 1H), 0.70(m, 4H). MS APCI, m/z=366.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-ccb5a348544b4c9fbbd7e501bdb28de7
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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