Water → HCID 86731316, compound

HRID 2277243Notes

Reaction equation

HRID 2277243 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]([C:17]2[CH:22]=[C:21]([F:23])[C:20]([O:24][CH2:25][CH:26]3[CH2:28][CH2:27]3)=[CH:19][N:18]=2)=[O:16])=[C:10](Cl)[CH:9]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.[Cu]I>[CH:26]1([CH2:25][O:24][C:20]2[C:21]([F:23])=[CH:22][C:17]([C:15]3[O:16][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)=[N:18][CH:19]=2)[CH2:28][CH2:27]1

Participants

6

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 86731317HCID 86731317, compound

Product 1

HCID 86731316HCID 86731316, compoundYield 5.9%

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)-5-(cyclopropylmethoxy)-4-fluoropyridine-2-carboxamide (1.05 g), potassium carbonate (664 mg) and copper(I) iodide (46.0 mg) in DMF (10 mL) was stirred at 160° C. for 1.5 hr. 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 chromatography (NH, ethyl acetate). The solvent was evaporated, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (56.9 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. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-13614be70194482a89444c398ec4b097
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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