Triethylamine → {4-[3-Cyclohexyl-3-(2-phenyl-2H-indazol-3-yl)-ureido]-3-fluoro-phenoxy}-acetic acid methyl ester

HRID 1690558Notes

Reaction equation

HRID 1690558 reaction equation
[CH:1]1([NH:7][C:8]2[N:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:10]=[C:11]3[C:16]=2[CH:15]=[CH:14][CH:13]=[CH:12]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:23][O:24][C:25](=[O:38])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]=[C:35]=[O:36])=[C:30]([F:37])[CH:29]=1.CCN(CC)CC>ClCCCl>[CH3:23][O:24][C:25](=[O:38])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35]([N:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:8]2[N:9]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:10]=[C:11]3[C:16]=2[CH:15]=[CH:14][CH:13]=[CH:12]3)=[O:36])=[C:30]([F:37])[CH:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12318206N-Cyclohexyl-2-phenyl-2H-indazol-3-amineHCID 86640266(3-Fluoro-4-isocyanato-phenoxy)-acetic acid methyl ester

Product 1

HCID 66905457{4-[3-Cyclohexyl-3-(2-phenyl-2H-indazol-3-yl)-ureido]-3-fluoro-phenoxy}-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In analogy to the procedure described in example 1.2, cyclohexyl-(2-phenyl-2H-indazol-3-yl)-amine (example 1.1) was reacted with (3-fluoro-4-isocyanato-phenoxy)-acetic acid methyl ester in 1,2-dichloroethane in the presence of Et3N (1.4 eq.) for 2 days under reflux conditions to give the title compound as yellow solid. MS: m/e=516.8 [M+H+].

Sources & evidence

ORD record
ord-21fd13ae07c0480f9f8adc0582874415
Source dataset
uspto-grants-2012_04
Patent number
US08153663B2

Reaction notes

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