Water → HCID 86731218, compound

HRID 2277165Notes

Reaction equation

HRID 2277165 reaction equation
Cl[C:2]1[C:7]([NH:8][C:9](=[O:21])[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH:18]3[CH2:20][CH2:19]3)=[CH:12][CH:11]=2)=[CH:6][N:5]=[C:4]([O:22][CH2:23][C@@H:24]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH3:25])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.[Cu]I>[CH:18]1([CH2:17][O:16][C:13]2[CH:14]=[CH:15][C:10]([C:9]3[O:21][C:2]4[CH:3]=[C:4]([O:22][CH2:23][C@@H:24]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH3:25])[N:5]=[CH:6][C:7]=4[N:8]=3)=[CH:11][CH:12]=2)[CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 86731219tert-butyl ((2S)-1-((4-chloro-5-((4-(cyclopropylmethoxy)benzoyl)amino)pyridin-2-yl)oxy)propan-2-yl)carbamate

Product 1

HCID 86731218HCID 86731218, compoundYield 35.1%

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 tert-butyl ((2S)-1-((4-chloro-5-((4-(cyclopropylmethoxy)benzoyl)amino)pyridin-2-yl)oxy)propan-2-yl)carbamate (500 mg), potassium carbonate (290 mg) and copper(I) iodide (20.0 mg) in DMF (10 mL) was stirred at 160° C. for 5 hr and 30 min 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 (162 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-73bcef3e18f8482185cedfc5810f1917
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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