HCID 86732302, compound → 1-((4-Cyanophenyl)-(2-ethoxy-6-oxo-4-(thiophen-2-yl)cyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)-urea

HRID 517190Notes

Reaction equation

HRID 517190 reaction equation
[C:1]([C:3]1C=CC(C(C2C(=O)CC(C(F)(F)F)CC=2OCC)NC(NC2C=CC=C(C(F)(F)F)C=2)=O)=CC=1)#N.[C:38]([C:40]1[CH:45]=[CH:44][C:43]([CH:46]([C:61]2[C:66](=[O:67])[CH2:65][CH:64]([C:68]3[S:69][CH:70]=[CH:71][CH:72]=3)[CH2:63][C:62]=2[OH:73])[NH:47][C:48]([NH:50][C:51]2[CH:56]=[CH:55][CH:54]=[C:53]([C:57]([F:60])([F:59])[F:58])[CH:52]=2)=[O:49])=[CH:42][CH:41]=1)#[N:39]>>[C:38]([C:40]1[CH:45]=[CH:44][C:43]([CH:46]([C:61]2[C:62](=[O:73])[CH2:63][CH:64]([C:68]3[S:69][CH:70]=[CH:71][CH:72]=3)[CH2:65][C:66]=2[O:67][CH2:1][CH3:3])[NH:47][C:48]([NH:50][C:51]2[CH:56]=[CH:55][CH:54]=[C:53]([C:57]([F:60])([F:59])[F:58])[CH:52]=2)=[O:49])=[CH:42][CH:41]=1)#[N:39]

Participants

3

Reactant 2

HCID 86732302HCID 86732302, compound2×HCID 867323081-((4-Cyanophenyl)(2-hydroxy-6-oxo-4-(thiophen-2-yl)cyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea2×

Product 1

HCID 867323091-((4-Cyanophenyl)-(2-ethoxy-6-oxo-4-(thiophen-2-yl)cyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)-urea

Procedure

The title compound is prepared in analogy to 1-((4-cyanophenyl)(2-ethoxy-6-oxo-4-(tri-fluoromethyl)cyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea (intermediate 13), using 1-((4-cyanophenyl)(2-hydroxy-6-oxo-4-(thiophen-2-yl)cyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea (intermediate 20, 444 mg, 0.87 mmol) as starting material. Yield: 507 mg; ESI mass spectrum [N+H]+=540, Retention time HPLC: 1.29 min (V011_S01).

Workup

  1. custom1.29 min (V011_S01)

Sources & evidence

ORD record
ord-91f4582ffd654261b1ae7c7d120c1382
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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