Triethylamine → 3-Chloro-4-{3-[2-(4-chloro-phenyl)-2H-indazol-3-yl]-3-cyclobutyl-ureido}-benzoic acid methyl ester

HRID 1690575Notes

Reaction equation

HRID 1690575 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([NH:17][CH:18]3[CH2:21][CH2:20][CH2:19]3)=[C:15]3[C:10]([CH:11]=[CH:12][CH:13]=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1.[CH3:22][O:23][C:24](=[O:35])[C:25]1[CH:30]=[CH:29][C:28]([N:31]=[C:32]=[O:33])=[C:27]([Cl:34])[CH:26]=1.CCN(CC)CC>ClCCCl>[CH3:22][O:23][C:24](=[O:35])[C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32]([N:17]([C:16]2[N:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:9]=[C:10]3[C:15]=2[CH:14]=[CH:13][CH:12]=[CH:11]3)[CH:18]2[CH2:21][CH2:20][CH2:19]2)=[O:33])=[C:27]([Cl:34])[CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66905392[2-(4-Chloro-phenyl)-2H-indazol-3-yl]-cyclobutyl-amineHCID 866402623-Chloro-4-isocyanato-benzoic acid methyl ester

Product 1

HCID 669053893-Chloro-4-{3-[2-(4-chloro-phenyl)-2H-indazol-3-yl]-3-cyclobutyl-ureido}-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In analogy to the procedure described in example 1.2, [2-(4-chloro-phenyl)-2H-indazol-3-yl]-cyclobutyl-amine was reacted with 3-chloro-4-isocyanato-benzoic acid methyl ester (example 9.1) in 1,2-dichloroethane in the presence of Et3N (3 eq.) for 3 days under reflux conditions to give the title compound as yellow oil. MS: m/e=509.4 [M+H+].

Sources & evidence

ORD record
ord-cbebb77e5fc44d66bc6ea75b26a53235
Source dataset
uspto-grants-2012_04
Patent number
US08153663B2

Reaction notes

Loading…