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

HRID 1690573Notes

Reaction equation

HRID 1690573 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([NH:17][CH:18]3[CH2:23][CH2:22][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.[CH3:24][O:25][C:26](=[O:39])[CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([N:35]=[C:36]=[O:37])=[C:31]([F:38])[CH:30]=1.CCN(CC)CC>ClCCCl>[CH3:24][O:25][C:26](=[O:39])[CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:36]([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[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:37])=[C:31]([F:38])[CH:30]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66905444[2-(4-Chloro-phenyl)-2H-indazol-3-yl]cyclohexyl-amineHCID 86640266(3-Fluoro-4-isocyanato-phenoxy)-acetic acid methyl ester

Product 1

HCID 45111329(4-{3-[2-(4-Chloro-phenyl)-2H-indazol-3-yl]-3-cyclohexyl-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, [2-(4-chloro-phenyl)-2H-indazol-3-yl]-cyclohexyl-amine (example 9.1) was reacted with (3-fluoro-4-isocyanato-phenoxy)-acetic acid methyl ester (example 24.1) in 1,2-dichloroethane in the presence of Et3N (2.2 eq.) for 3 days under reflux conditions to give the title compound as brown gum. MS: m/e=551.3 [M+H+].

Sources & evidence

ORD record
ord-e762ecf8810d4c0682f7f8596d6babb5
Source dataset
uspto-grants-2012_04
Patent number
US08153663B2

Reaction notes

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