Trifluoroacetic acid → 4-(4-(3-(4-Chloro-3-(trifluoromethyl)phenyl)ureido)-3-fluorophenoxy)picolinic acid

HRID 409712Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:32])[NH:10][C:11]2[CH:30]=[CH:29][C:14]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]([O:24]C(C)(C)C)=[O:23])[CH:17]=3)=[CH:13][C:12]=2[F:31])=[CH:4][C:3]=1[C:33]([F:36])([F:35])[F:34].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:32])[NH:10][C:11]2[CH:30]=[CH:29][C:14]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]([OH:24])=[O:23])[CH:17]=3)=[CH:13][C:12]=2[F:31])=[CH:4][C:3]=1[C:33]([F:35])([F:36])[F:34]

Participants

Conditions

Temperature: 50 °C

Procedure

At room temperature, tert-butyl 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)-3-fluorophenoxy)picolinate (1.8 g, 3.43 mmol) was dissolved in dichloromethane (15 mL). Trifluoroacetic acid (15 mL) and triethyl silane (0.2 mL) was added. The resulted mixture was heated to 50° C. and stirred for 16 h. The solvent was removed under reduced pressure. The residue was partitioned in water (50 mL) and ethyl acetate (50 mL), and separated. The organic phase was removed, and the aqueous layer was filtered. The solid was washed with water (20 mL×2) and dried in vacuum to give the title compound (1.48 g, purity 85%, yield 92%) as a grey solid.

Workup

customThe solvent was removed under reduced pressure
customThe residue was partitioned in water (50 mL)
customethyl acetate (50 mL), and separated
customThe organic phase was removed
filtrationthe aqueous layer was filtered
washThe solid was washed with water (20 mL×2)
customdried in vacuum

Sources & evidence

ORD record: ord-b1935a8e1c6e49dd9057793c89058064
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759531B2

Reaction notes

Loading…