4-Chlorophenylboronic acid → 4-amino-8-(4-chlorophenyl)-N-cyclobutyl-cinnoline-3-carboxamide

HRID 2375703Notes

Reaction equation

HRID 2375703 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].[Cl:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:24]3[CH:25]=[CH:26][C:21]([Cl:20])=[CH:22][CH:23]=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 742994-Chlorophenylboronic acidHCID 672284794-amino-8-bromo-N-cyclobutyl-cinnoline-3-carboxamide

Product 1

HCID 236298534-amino-8-(4-chlorophenyl)-N-cyclobutyl-cinnoline-3-carboxamideYield 70.3%

Procedure

Using Method A, 4-amino-8-bromo-N-cyclobutyl-cinnoline-3-carboxamide (145 mg) and 4-chlorophenyl boronic acid (176 mg) were reacted to afford the title compound (112 mg) as white solid. 1H NMR (500 MHz, DMSO-d6) δ 9.31 (d, 1H), 8.43 (d, 1H), 7.86 (m, 1H), 7.79 (m, 1H), 7.73 (m, 2H), 7.54 (m, 2H), 4.52 (m, 1H), 2.26-2.10(m, 4H), 1.72-1.62 (m, 2H). MS APCI, m/z=353 (M+H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-f1faa4aa2ae5451a95a61e5b4c77a484
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

Loading…