1-(2-(3-(1-Hydroxycyclopent-3-enyl)phenoxy)pyridin-3-yl)-3-(4-(trifluoromethoxy)phenyl)urea → HCID 68527407, compound

HRID 132611Notes

Reaction equation

HRID 132611 reaction equation
O[C:2]1([C:7]2[CH:8]=[C:9]([CH:32]=[CH:33][CH:34]=2)[O:10][C:11]2[C:16]([NH:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=3)=[O:19])=[CH:15][CH:14]=[CH:13][N:12]=2)[CH2:6][CH:5]=[CH:4][CH2:3]1.OC(C1C=C(C=CC=1)OC1C(NC(NC2C=CC(OC(F)(F)F)=CC=2)=O)=CC=CN=1)(CC=C)CC=C>CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.ClCCl>[CH:2]1([C:7]2[CH:8]=[C:9]([CH:32]=[CH:33][CH:34]=2)[O:10][C:11]2[C:16]([NH:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=3)=[O:19])=[CH:15][CH:14]=[CH:13][N:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 685278831-(2-(3-(1-Hydroxycyclopent-3-enyl)phenoxy)pyridin-3-yl)-3-(4-(trifluoromethoxy)phenyl)ureaHCID 685297861-(2-(3-(4-Hydroxyhepta-1,6-dien-4-yl)phenoxy)pyridin-3-yl)-3-(4-(trifluoromethoxy)phenyl)urea

Product 1

HCID 68527407HCID 68527407, compound

Reagents, catalysts & solvents 2

HCID 11147261(1,3-Dimesitylimidazolidin-2-ylidene)(tricyclohexylphosphine)benzylidene ruthenium dichlorideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

1-(2-(3-(1-hydroxycyclopent-3-enyl)phenoxy)pyridin-3-yl)-3-(4-(trifluoromethoxy)phenyl)urea: A mixture of Example 640 (125 mg, 0.25 mmol) and Grubb's second generation catalyst (0.6 mg) in dichloromethane (70 mL) was stirred at rt for 16 h. An additional 1.0 mg of Grubb's second generation catalyst was added and the mixture was stirred at rt for an additional 17 h. Evaporation under reduced pressure afforded a residue which was filtered and purified using reverse-phase preparative HPLC. (M+H)+=472.

Workup

  1. customEvaporation under reduced pressure
  2. customafforded a residue which
  3. filtrationwas filtered
  4. custompurified

Sources & evidence

ORD record
ord-4f0a761f324e433fad2366a03414ca74
Source dataset
uspto-grants-2008_06
Patent number
US07388021B2

Reaction notes

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