3,5-Dimethylphenylboronic acid → 4-amino-N-cyclobutyl-8-(3,5-dimethylphenyl)cinnoline-3-carboxamide

HRID 2375702Notes

Reaction equation

HRID 2375702 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[CH2:19][CH2:18][CH2:17]1)=[O:14].[CH3:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[C:25]([CH3:27])[CH:26]=1>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:23]3[CH:24]=[C:25]([CH3:27])[CH:26]=[C:21]([CH3:20])[CH:22]=3)[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH:16]1[CH2:19][CH2:18][CH2:17]1)=[O:14]

Participants

3

Reactant 2

HCID 27343493,5-Dimethylphenylboronic acidHCID 672284794-amino-8-bromo-N-cyclobutyl-cinnoline-3-carboxamide

Product 1

HCID 251834124-amino-N-cyclobutyl-8-(3,5-dimethylphenyl)cinnoline-3-carboxamideYield 37.7%

Procedure

Using Method A, 4-amino-8-bromo-N-cyclobutyl-cinnoline-3-carboxamide (145 mg) and 3,5-dimethylphenyl boronic acid (169 mg) were reacted to afford the title compound (59 mg) as white solid. 1H NMR (500 MHz, DMSO-d6) δ 9.31 (d, 1H), 8.38 (d, 1H), 7.78 (m, 2H), 7.28 (s, 2H), 7.06 (s, 1H), 4.52 (m, 1H), 2.35 (s, 6H), 2.26-2.10(m, 4H), 1.72-1.62 (m, 2H). MS APCI, m/z=347 (M+H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-9e4804167c934ef48e6e0b1470f56d4b
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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