1-((4-Cyano-2-fluorophenyl)(2-ethoxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea → 1-((4-Bromo-2-methoxyphenyl)(2-ethoxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)-urea

HRID 517217Notes

Reaction equation

HRID 517217 reaction equation
[C:1]([C:3]1C=CC(C(C2C(=O)CCCC=2OCC)NC(NC2C=CC=C(C(F)(F)F)C=2)=O)=C(F)C=1)#N.[Br:35][C:36]1[CH:41]=[CH:40][C:39]([CH:42]([C:57]2[C:62](=[O:63])[CH2:61][CH2:60][CH2:59][C:58]=2[OH:64])[NH:43][C:44]([NH:46][C:47]2[CH:52]=[CH:51][CH:50]=[C:49]([C:53]([F:56])([F:55])[F:54])[CH:48]=2)=[O:45])=[C:38]([O:65][CH3:66])[CH:37]=1>>[Br:35][C:36]1[CH:41]=[CH:40][C:39]([CH:42]([C:57]2[C:58](=[O:64])[CH2:59][CH2:60][CH2:61][C:62]=2[O:63][CH2:1][CH3:3])[NH:43][C:44]([NH:46][C:47]2[CH:52]=[CH:51][CH:50]=[C:49]([C:53]([F:55])([F:54])[F:56])[CH:48]=2)=[O:45])=[C:38]([O:65][CH3:66])[CH:37]=1

Participants

3

Reactant 2

HCID 867323301-((4-Cyano-2-fluorophenyl)(2-ethoxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea2×HCID 867323351-((4-Bromo-2-methoxyphenyl)(2-hydroxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea2×

Product 1

HCID 867323361-((4-Bromo-2-methoxyphenyl)(2-ethoxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)-urea

Procedure

The title compound is prepared in analogy to 1-((4-cyano-2-fluorophenyl)(2-ethoxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea (intermediate 41) using ici 1-((4-bromo-2-methoxyphenyl)(2-hydroxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea (intermediate 48, 900 mg, 1.75 mmol) as starting material. Yield: 910 mg; ESI mass spectrum [(79Br)-M+H]+=541, [(81Br)-M+H]+=543; Retention time HPLC: 0.92 min (Z011_S03).

Sources & evidence

ORD record
ord-54cfe9296ef5419396752815c5857a65
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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