5-[4-(Trifluoromethyl)phenyl]-1,3-cyclohexanedione → HCID 86732304, compound

HRID 517185Notes

Reaction equation

HRID 517185 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9](C2C(=O)CC(C(F)(F)F)CC=2O)[NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=[O:12])=[CH:5][CH:4]=1)#[N:2].[F:36][C:37]([F:53])([F:52])[C:38]1[CH:43]=[CH:42][C:41]([CH:44]2[CH2:49][C:48](=[O:50])[CH2:47][C:46](=[O:51])[CH2:45]2)=[CH:40][CH:39]=1>>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:47]2[C:46](=[O:51])[CH2:45][CH:44]([C:41]3[CH:40]=[CH:39][C:38]([C:37]([F:52])([F:53])[F:36])=[CH:43][CH:42]=3)[CH2:49][C:48]=2[OH:50])[NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:23])[F:22])[CH:15]=2)=[O:12])=[CH:5][CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 5991275-[4-(Trifluoromethyl)phenyl]-1,3-cyclohexanedioneHCID 86732301HCID 86732301, compound2×

Product 1

HCID 86732304HCID 86732304, compound

Procedure

The title compound is prepared in analogy to 1-((4-cyanophenyl)(2-hydroxy-6-oxo-4-(tri-fluoromethyl)cyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea (intermediate 12), using 5-(4-(trifluoromethyl)phenyl)cyclohexane-1,3-dione (500 mg, 1.95 mmol) as starting material. Yield: 930 mg; ESI mass spectrum [M+H]+=574, Retention time HPLC: 0.85 min (V011_S01).

Workup

  1. custom0.85 min (V011_S01)

Sources & evidence

ORD record
ord-03d5392d4f084a3c848901834d008f47
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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