HCID 10114545, compound → HCID 10204152, compound

HRID 2182476Notes

Reaction equation

HRID 2182476 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:33])[C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH:20]=[CH:19][CH:18]([C:21]3[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=3)[O:17]2)=[CH:12][CH:11]=1>CCOC(C)=O.O=[Pt]=O>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:33])[C:10]1[CH:11]=[CH:12][C:13]([CH:16]2[CH2:20][CH2:19][CH:18]([C:21]3[CH:22]=[C:23]([O:31][CH3:32])[C:24]([O:29][CH3:30])=[C:25]([O:27][CH3:28])[CH:26]=3)[O:17]2)=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 10114545HCID 10114545, compound

Product 1

HCID 10204152HCID 10204152, compoundYield 229.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a degazed solution of 289 (43 mg, 0.096 mmol) in AcOEt (4 mL) was added PtO2 (3 mg, 0.01 mmol) and the reaction mixture was stirred at room temperature under a 1 atm pressure of H2 for 16 h. The reaction flask was purged with N2 then the reaction mixture was filtered through celite, rinsed with MeOH and concentrated. The crude residue was purified three times by flash chromatography on silica gel (MeOH/DCM: 2/98, AcOEt/DCM: 30/70 and AcOEt/CHCl3: 30/70) to afford the title compound 290 (10 mg, 0.22 mmol, 23% yield). 1H NMR (CDCl3) δ (ppm): 8.10 (s, 1H), 7.91 (d, J=8.0 Hz, 2H), 7.50 (d, J=8.0 Hz, 2H), 7.34 (d, J=7.5 Hz, 1H), 7.10 (t, J=7.5 Hz, 1H), 6.96-6.85 (m, 2H), 6.64 (s, 2H), 5.33 (t, J=7.0 Hz, 1H), 5.21 (t, J=7.0 Hz, 1H), 3.89 (s, 6H), 3.85 (s, 3H), 2.59-2.40 (m, 2H), 2.09-1.88 (m, 2H).

Workup

  1. customThe reaction flask was purged with N2
  2. filtrationthe reaction mixture was filtered through celite
  3. washrinsed with MeOH
  4. concentrationconcentrated
  5. customThe crude residue was purified three times by flash chromatography on silica gel (MeOH/DCM: 2/98, AcOEt/DCM: 30/70 and AcOEt/CHCl3: 30/70)

Sources & evidence

ORD record
ord-8894424ce39345ec9d36e9099e596e57
Source dataset
uspto-grants-2005_05
Patent number
US06897220B2

Reaction notes

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