Ethyl Acetate → HCID 86731305, compound

HRID 2277233Notes

Reaction equation

HRID 2277233 reaction equation
Cl[C:2]1[C:7]([NH:8][C:9](=[O:24])[C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH2:19][CH:20]3[CH2:22][CH2:21]3)=[C:12]([F:23])[CH:11]=2)=[CH:6][N:5]=[C:4]([O:25][CH2:26][C@@H:27]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH3:28])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C.[Cu]I>[CH:20]1([CH2:19][O:18][C:13]2[C:14]([O:16][CH3:17])=[CH:15][C:10]([C:9]3[O:24][C:2]4[CH:3]=[C:4]([O:25][CH2:26][C@@H:27]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH3:28])[N:5]=[CH:6][C:7]=4[N:8]=3)=[CH:11][C:12]=2[F:23])[CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 86731306HCID 86731306, compound

Product 1

HCID 86731305HCID 86731305, compoundYield 24.7%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of tert-butyl ((2S)-1-((4-chloro-5-((4-(cyclopropylmethoxy)-3-fluoro-5-methoxybenzoyl)amino)pyridin-2-yl)oxy)propan-2-yl)carbamate (5.87 g), potassium carbonate (3.10 g) and copper(I) iodide (213 mg) in DMF. (40 mL) was stirred at 150° C. for 1 hr, and then at 160° C. for 3 hr. The reaction mixture was subjected to silica gel chromatography (NH, ethyl acetate), and washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (1.35 g).

Workup

  1. waitat 160° C. for 3 hr
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ef74287535bc4cff96d78145ca464226
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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