1-((4-Cyanophenyl)(2-methoxy-6-oxocyclohex-1-enyl)methyl)-3-(4-(trifluoromethyl)pyridin-2-yl)urea → 1-((5-Cyanopyridin-2-yl)(2-methoxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea

HRID 517198Notes

Reaction equation

HRID 517198 reaction equation
[C:1](C1C=CC(C(C2C(=O)CCCC=2OC)NC(NC2C=C(C(F)(F)F)C=CN=2)=O)=CC=1)#N.[C:33]([C:35]1[CH:36]=[CH:37][C:38]([CH:41]([C:56]2[C:61](=[O:62])[CH2:60][CH2:59][CH2:58][C:57]=2[OH:63])[NH:42][C:43]([NH:45][C:46]2[CH:51]=[CH:50][CH:49]=[C:48]([C:52]([F:55])([F:54])[F:53])[CH:47]=2)=[O:44])=[N:39][CH:40]=1)#[N:34]>>[C:33]([C:35]1[CH:36]=[CH:37][C:38]([CH:41]([C:56]2[C:57](=[O:63])[CH2:58][CH2:59][CH2:60][C:61]=2[O:62][CH3:1])[NH:42][C:43]([NH:45][C:46]2[CH:51]=[CH:50][CH:49]=[C:48]([C:52]([F:54])([F:55])[F:53])[CH:47]=2)=[O:44])=[N:39][CH:40]=1)#[N:34]

Participants

3

Reactant 2

HCID 867323131-((4-Cyanophenyl)(2-methoxy-6-oxocyclohex-1-enyl)methyl)-3-(4-(trifluoromethyl)pyridin-2-yl)urea2×HCID 867323171-((5-Cyanopyridin-2-yl)(2-hydroxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea2×

Product 1

HCID 867323181-((5-Cyanopyridin-2-yl)(2-methoxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea

Procedure

The title compound is prepared in analogy to 1-((4-cyanophenyl)(2-methoxy-6-oxocyclohex-1-enyl)methyl)-3-(4-(trifluoromethyl)pyridin-2-yl)urea (intermediate 25) using 1-((5-cyanopyridin-2-yl)(2-hydroxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl) urea (intermediate 28, 330 mg, 0.767 mmol) as starting material. Yield: 203 mg; ESI mass spectrum [M+H]+=445, Retention time HPLC: 1.05 min (V011_S01).

Workup

  1. custom1.05 min (V011_S01)

Sources & evidence

ORD record
ord-2772977974054828a8dfe5266567a1df
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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