HCID 58392087, compound → HCID 58392316, compound

HRID 561405Notes

Reaction equation

HRID 561405 reaction equation
[CH3:1][C:2]1(C)OC(=O)[CH: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)[C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=2)[C:4](=[O:32])[O:3]1>N1C=CC=CC=1.C(O)C.[Cu]>[CH3:31][S:30][CH2:29][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:23]=1[NH:22][CH:21]=[C:20]2[CH:9]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)[CH2:5][C:4]([O:3][CH2:2][CH3:1])=[O:32]

Participants

5

Reactant 1

HCID 58392087HCID 58392087, compound

Product 1

HCID 58392316HCID 58392316, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

1.2 mg (0.02 mmol) of copper powder were added to 882 mg (1.92 mmol) of the compound from Example 20A in 15 ml of pyridine and 5 ml of ethanol. The reaction mixture was heated under reflux for 2 h. It was concentrated, and the crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient) and preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient) to result in 635 mg (82% of theory) of the title compound.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. concentrationIt was concentrated
  4. customthe crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient) and preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-a8b533659cdc4a01a559a079d016f582
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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