4-Methoxypyridine-3-boronic acid → 4-amino-N-cyclopropyl-8-(4-methoxypyridin-3-yl)cinnoline-3-carboxamide

HRID 2375716Notes

Reaction equation

HRID 2375716 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[CH:26]=[CH:25][N:24]=[CH:23][C:22]=1B(O)O>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][C:21]=3[O:20][CH3:19])[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 27625564-Methoxypyridine-3-boronic acidHCID 672292774-amino-8-bromo-N-cyclopropylcinnoline-3-carboxamide

Product 1

HCID 597915634-amino-N-cyclopropyl-8-(4-methoxypyridin-3-yl)cinnoline-3-carboxamideYield 33%

Procedure

Using Method A, 4-amino-8-bromo-N-cyclopropyl-cinnoline-3-carboxamide (143 mg, 0.47 mmol) and 4-methoxypyridine-3-boronic acid (640 mg, 4.20 mmol) were reacted. After purification the title compound (52 mg, 33% yield) was obtained as a white solid. 1H NMR (500 MHz, CDCl3) δ 8.58 (d, J=5.8 Hz, 1H), 8.57 (bm, 1H), 8.44 (s, 1H), 7.91 (m, 1H), 7.74 (m, 2H), 6.94 (d, J=5.8 Hz, 1H), 3.77 (s, 3H), 2.96 (m, 1H), 0.86 (m, 2H), 0.64 (m, 2H). MS APCI, m/z=336.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-e130b14fe3964011879749a02d344ac2
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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