HCID 59293936, compound → HCID 58392151, compound

HRID 561389Notes

Reaction equation

HRID 561389 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:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][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:11]=[CH:12][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:14][CH:15]=1)[CH2:5][C:4]([O:3][CH2:2][CH3:1])=[O:32]

Participants

5

Reactant 1

HCID 59293936HCID 59293936, compound

Product 1

HCID 58392151HCID 58392151, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

0.7 mg (0.01 mmol) of copper powder was added to 504 mg (1.06 mmol) of the compound from Example 12A in 8 ml of pyridine and 2 ml of ethanol. The reaction mixture was heated under reflux for 1 h. It was concentrated, and the crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 241 mg (54% of theory) of the title compound.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 1 h
  3. concentrationIt was concentrated
  4. customthe crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Sources & evidence

ORD record
ord-38fec432d24c48d0a1271f0cd9be18fa
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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