Water → HCID 86731226, compound

HRID 2277171Notes

Reaction equation

HRID 2277171 reaction equation
[C:1]([NH:4][C@@H:5]([CH3:30])[CH2:6][O:7][C:8]1[N:13]=[CH:12][C:11]([NH:14][C:15](=[O:28])[C:16]2[CH:21]=[C:20]([F:22])[C:19]([O:23][CH2:24][CH:25]3[CH2:27][CH2:26]3)=[N:18][CH:17]=2)=[C:10](Cl)[CH:9]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.[Cu]I>[CH:25]1([CH2:24][O:23][C:19]2[N:18]=[CH:17][C:16]([C:15]3[O:28][C:10]4[CH:9]=[C:8]([O:7][CH2:6][C@@H:5]([NH:4][C:1](=[O:3])[CH3:2])[CH3:30])[N:13]=[CH:12][C:11]=4[N:14]=3)=[CH:21][C:20]=2[F:22])[CH2:27][CH2:26]1

Participants

6

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 86731227HCID 86731227, compound

Product 1

HCID 86731226HCID 86731226, compoundYield 5%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
160 °C

Procedure

A suspension of N-(6-(((2S)-2-acetamidopropyl)oxy)-4-chloropyridin-3-yl)-6-(cyclopropylmethoxy)-5-fluoronicotinamide (860 mg), potassium carbonate (544 mg) and copper(I) iodide (37.5 mg) in DMF (10 mL) was stirred at 160° C. for 3 hr under microwave irradiation. To the reaction mixture was added water, and the obtained mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and subjected to silica gel column chromatography (NH, ethyl acetate). The solvent was evaporated, and the obtained solid was washed with ethyl acetate/hexane to give the title compound (39.8 mg).

Workup

  1. extractionthe obtained mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. customThe solvent was evaporated
  4. washthe obtained solid was washed with ethyl acetate/hexane

Sources & evidence

ORD record
ord-87cd803c34774a9692e324ae5a55cc4e
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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