HCID 58392401, compound → HCID 58392239, compound

HRID 561438Notes

Reaction equation

HRID 561438 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH:9]([C:20]2[C:28]3[C:23](=[C:24]([CH2:29][S:30][CH3:31])[CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)[CH:10]2C(=O)O[C:13](C)([CH3:17])[O:12][C:11]2=[O:19])=[C:4]([F:32])[CH:3]=1>N1C=CC=CC=1.C(O)C.[Cu]>[Cl:1][C:2]1[CH:3]=[C:4]([F:32])[C:5]([CH:9]([C:20]2[C:28]3[C:23](=[C:24]([CH2:29][S:30][CH3:31])[CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)[CH2:10][C:11]([O:12][CH2:13][CH3:17])=[O:19])=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 1

HCID 58392401HCID 58392401, compound

Product 1

HCID 58392239HCID 58392239, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

11 mg (166 μmol) of copper powder were added to a solution of 1.60 g (3.33 mmol) of the compound from Example 96A in 6 ml of pyridine and 1.3 ml of ethanol. The reaction mixture was heated under reflux for 4 h. It was concentrated, and the crude product was purified firstly by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 5/1) and then by preparative HPLC (mobile phase: acetonitrile/water gradient). 1.15 g (81% of theory) of the title compound were obtained.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 4 h
  3. concentrationIt was concentrated
  4. customthe crude product was purified firstly by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 5/1)

Sources & evidence

ORD record
ord-82c42b64cd1d40a9b58ea25cde0dd492
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

Loading…