HCID 67976021, compound → HCID 67976211, compound

HRID 508619Notes

Reaction equation

HRID 508619 reaction equation
[CH2:1]([O:3][C:4](=[O:29])/[CH:5]=[CH:6]/[C:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[N:9]([C:19]2[CH:24]=[CH:23][C:22]([S:25](=[O:28])(=[O:27])[NH2:26])=[CH:21][CH:20]=2)[N:8]=1)[CH3:2]>CCOC(C)=O.[Pd]>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][C:7]1[CH:11]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=2)[N:9]([C:19]2[CH:20]=[CH:21][C:22]([S:25](=[O:27])(=[O:28])[NH2:26])=[CH:23][CH:24]=2)[N:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 67976021HCID 67976021, compound

Product 1

HCID 67976211HCID 67976211, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 16c (0.13 g, 0.32 mmol) in 5 mL of EtOAc was added 10% palladium on carbon. The solution was filled with H2 and the reaction mixture was stirred for 2 hours. After the solution was filtered through Celite, the filtrate was concentrated in vacuo. Purification by column chromatography (3:7 EtOAc-haxanes) gave the title compound, 0.11 g (84%) as a white solid. mp 116.5-117.2° C. 1H NMR (300 MHz, CDCl3): δ 7.79 (d, J=9 Hz, 2H), 7.36 (d, J=9 Hz, 2H), 7.17-7.04 (m, 4H), 6.32 (s, 1H), 5.23 (s, 2H), 4.17 (q, J=7 Hz, 2H), 3.05 (t, J=8 Hz, 2H), 2.76 (t, J=8 Hz, 2H), 2.35 (s, 3H), 1.26 (t, J=7 Hz, 3H).

Workup

  1. additionThe solution was filled with H2
  2. filtrationAfter the solution was filtered through Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. customPurification by column chromatography (3:7 EtOAc-haxanes)

Sources & evidence

ORD record
ord-e2cda2df16224b75955dddb47c06a4ec
Source dataset
uspto-grants-2015_08
Patent number
US09096532B2

Reaction notes

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