Water → HCID 86731266, compound

HRID 2277205Notes

Reaction equation

HRID 2277205 reaction equation
Cl[C:2]1[C:7]([NH:8][C:9](=[O:23])[C:10]2[CH:15]=[C:14]([F:16])[C:13]([O:17][CH2:18][CH:19]3[CH2:21][CH2:20]3)=[CH:12][C:11]=2[F:22])=[CH:6][N:5]=[C:4]([O:24][CH2:25][C@@H:26]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH3:27])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.[Cu]I>[CH:19]1([CH2:18][O:17][C:13]2[C:14]([F:16])=[CH:15][C:10]([C:9]3[O:23][C:2]4[CH:3]=[C:4]([O:24][CH2:25][C@@H:26]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH3:27])[N:5]=[CH:6][C:7]=4[N:8]=3)=[C:11]([F:22])[CH:12]=2)[CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 86731267tert-butyl ((2S)-1-((4-chloro-5-((4-(cyclopropylmethoxy)-2,5-difluorobenzoyl)amino)pyridin-2-yl)oxy)propan-2-yl)carbamate

Product 1

HCID 86731266HCID 86731266, compoundYield 32.8%

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)-2,5-difluorobenzoyl)amino)pyridin-2-yl)oxy)propan-2-yl)carbamate (5.39 g), potassium carbonate (2.91 g) and copper(I) iodide (201 mg) in DMF (30 mL) was stirred at 160° C. for 4 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 residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (1.64 g).

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-6eb55c3d8bb1466a855f316c036bc3e6
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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