Water → HCID 86731231, compound

HRID 2277177Notes

Reaction equation

HRID 2277177 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]([Cl: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>[Cl:22][C:20]1[CH:21]=[C:16]([C:15]2[O:28][C:10]3[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]=3[N:14]=2)[CH:17]=[N:18][C:19]=1[O:23][CH2:24][CH:25]1[CH2:27][CH2:26]1

Participants

6

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 86731232HCID 86731232, compound

Product 1

HCID 86731231HCID 86731231, compoundYield 18.3%

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-chloro-6-(cyclopropylmethoxy)nicotinamide (910 mg), potassium carbonate (555 mg) and copper(I) iodide (38.2 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 (153 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-3514d5b009404b6f891b2e45a93cbad1
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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