Water → HCID 59596915, compound

HRID 2265722Notes

Reaction equation

HRID 2265722 reaction equation
NC([C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]3([C:23]([NH:25][C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)=[O:24])[CH2:22][CH2:21]3)=[O:19])=[C:13]([F:33])[C:12]=2[F:34])[CH:7]=[CH:6][N:5]=1)=O.O.FC(F)(F)C(OI(C1C=CC=CC=1)OC(=O)C(F)(F)F)=O.[OH-].[Na+].C[N:60](C)C=O>N1C=CC=CC=1>[NH2:60][C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]3([C:23]([NH:25][C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)=[O:24])[CH2:21][CH2:22]3)=[O:19])=[C:13]([F:33])[C:12]=2[F:34])[CH:7]=[CH:6][N:5]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 59596965HCID 59596965, compound

Product 1

HCID 59596915HCID 59596915, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-(4-{[2-(Aminocarbonyl)pyridin-4-yl]oxy}-2,3-difluorophenyl)-N′-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide (295 mg) was dissolved in N,N-dimethylformamide (4 ml). Water (0.0563 ml), [bis(trifluoroacetoxy)iodo]benzene (536 mg) and pyridine (0.303 ml) were added thereto at room temperature in this order, followed by stirring for 25 hr and 10 min. The reaction was stopped by adding a 1N aqueous solution of sodium hydroxide (9 ml), and the reaction mixture was partitioned between ethyl acetate (30 ml) and water (10 ml). The organic layer was washed with water (30 ml) in twice, brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The resultant residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent; heptane:ethyl acetate=1:3), and fractions containing the target compound were concentrated under reduced pressure. The residue was dried under reduced pressure to provide the titled compound as a pale yellow solid (168.4 mg, 61%).

Workup

  1. customat room temperature
  2. customthe reaction mixture was partitioned between ethyl acetate (30 ml) and water (10 ml)
  3. washThe organic layer was washed with water (30 ml) in twice, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customThe resultant residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent; heptane:ethyl acetate=1:3), and fractions
  7. additioncontaining the target compound
  8. concentrationwere concentrated under reduced pressure
  9. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-3b25c23f2e9a4e18b5abfd2e4f6a9dff
Source dataset
uspto-grants-2010_12
Patent number
US07855290B2

Reaction notes

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