Trifluoroacetic acid → Sorafenib related compound 10

HRID 1522921Notes

Reaction equation

HRID 1522921 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:31])[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][CH:12]=2)=[CH:4][C:3]=1[C:32]([F:35])([F:34])[F:33].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:31])[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][CH:12]=2)=[CH:4][C:3]=1[C:32]([F:35])([F:33])[F:34]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 57541570HCID 57541570, compound

Product 1

HCID 59772925Sorafenib related compound 10Yield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

At room temperature, tert-butyl 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)phenoxy)picolinate (1.4 g, 2.76 mmol) was dissolved in dichloromethane (20 mL). To the resulted solution, trifluoroacetic acid (20 mL) and triethylsilane (0.5 mL) were added. The resulted mixture was heated to 50° C. and stirred for 16 hours. The solvent was removed under reduced pressure, and water (50 mL) and ethyl acetate (70 mL) were added. The resulted mixture was separated and the organic phase was removed. The aqueous layer was filtered and the solid was washed with water (30 mL×2). The solid was dried under vacuum to give the title compound (1.1 g, purity 97%, yield 90%) as a light green solid.

Workup

  1. customThe solvent was removed under reduced pressure, and water (50 mL) and ethyl acetate (70 mL)
  2. additionwere added
  3. customThe resulted mixture was separated
  4. customthe organic phase was removed
  5. filtrationThe aqueous layer was filtered
  6. washthe solid was washed with water (30 mL×2)
  7. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-1e94d92ce6f64588bbad6541f3c2e5ff
Source dataset
uspto-grants-2015_07
Patent number
US09078933B2

Reaction notes

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