5-Chloro-2-methylaniline → 2-Bromo-5-[(5-chloro-2-methyl-phenylamino)-(4-cyano-phenyl)-methyl]-1-isopropyl-1H-imidazole-4-carboxylic acid ethyl ester

HRID 2410099Notes

Reaction equation

HRID 2410099 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([Br:24])[N:9]([CH:21]([CH3:23])[CH3:22])[C:10]=1[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=1)O)=[O:5])[CH3:2].[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([CH3:33])=[C:30]([CH:32]=1)[NH2:31]>CCCCCC.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([Br:24])[N:9]([CH:21]([CH3:23])[CH3:22])[C:10]=1[CH:11]([NH:31][C:30]1[CH:32]=[C:26]([Cl:25])[CH:27]=[CH:28][C:29]=1[CH3:33])[C:13]1[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 72605-Chloro-2-methylanilineHCID 867077572-bromo-5-[(4-cyano-phenyl)-hydroxy-methyl]-1-isopropyl-1H-imidazole-4-carboxylic acid ethyl ester

Product 1

HCID 867077562-Bromo-5-[(5-chloro-2-methyl-phenylamino)-(4-cyano-phenyl)-methyl]-1-isopropyl-1H-imidazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The title compound was prepared in analogy to the procedure described for step E2 using 2-bromo-5-[(4-cyano-phenyl)-hydroxy-methyl]-1-isopropyl-1H-imidazole-4-carboxylic acid ethyl ester (step H3) and 5-chloro-2-methyl-aniline as starting materials. tR: 1.35 min (LC-MS 2); ESI-MS: 515.2 [M−H]+ (LC-MS 2); Rf=0.16 (hexane/ EtOAc, 3:1).

Sources & evidence

ORD record
ord-fba46484a78d4b4085f68615d79901bd
Source dataset
uspto-grants-2014_08
Patent number
US08815926B2

Reaction notes

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