3-Cyanophenylboronic acid → HCID 9868378, compound

HRID 2297632Notes

Reaction equation

HRID 2297632 reaction equation
[CH:1]([C:4]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[N:25]=[C:24]([CH3:26])[O:23][N:22]=3)[CH:16]=2)[C:7]2[C:8](=[O:12])[NH:9][CH:10]=[CH:11][C:6]=2[N:5]=1)([CH3:3])[CH3:2].[C:27]([C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1)#[N:28]>ClCCl>[CH:1]([C:4]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[N:25]=[C:24]([CH3:26])[O:23][N:22]=3)[CH:16]=2)[C:7]2[C:8](=[O:12])[N:9]([C:33]3[CH:32]=[CH:31][CH:30]=[C:29]([C:27]#[N:28])[CH:34]=3)[CH:10]=[CH:11][C:6]=2[N:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 27343253-Cyanophenylboronic acidHCID 15425478HCID 15425478, compound

Product 1

HCID 9868378HCID 9868378, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By reaction of 2-isopropyl-3-[3-(5-methyl-[1,2,4]oxadiazol-3-yl)benzyl]-3,5-dihydroimidazo[4,5-c]pyridin-4-one with 3-cyanophenylboronic acid under copper acetate catalysis in dichloromethane, 2-isopropyl-3-[3-(5-methyl-[1,2,4]oxadiazol-3-yl)benzyl]-5-(3-cyanophenyl)-3,5-dihydroimidazo[4,5-c]pyridin-4-one is obtained. By subsequent reaction in ethanol NaHCO3 and then with hydroxylammonium chloride, 2-isopropyl-3-[3-(5-methyl-[1,2,4]oxadiazol-3-yl)benzyl]-5-(3-N-hydroxyamidinophenyl)-3,5-dihydroimidazo[4,5-c]pyridin-4-one is obtained.

Sources & evidence

ORD record
ord-b767cd16200c46039026a48c88bb5975
Source dataset
uspto-grants-2002_12
Patent number
US06492384B1

Reaction notes

Loading…