HCID 86709972, compound → HCID 67992591, compound

HRID 508615Notes

Reaction equation

HRID 508615 reaction equation
[N:1]([CH2:4][C:5]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[N:7]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[N:6]=1)=[N+]=[N-]>CCOC(C)=O.[Pd]>[C:10]([C:8]1[N:7]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:21])=[O:22])=[CH:16][CH:15]=2)[N:6]=[C:5]([CH2:4][NH2:1])[CH:9]=1)([CH3:13])([CH3:11])[CH3:12]

Participants

4

Reactant 1

HCID 86709972HCID 86709972, compound

Product 1

HCID 67992591HCID 67992591, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 9h (0.4 g, 1.2 mmol) in 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 recrystallization with DCM/hexanes gave the title compound 10h, 0.35 g (95%) as a white solid. mp 137.5-145.1° C. 1H NMR (300 MHz, DMSO-d6): δ 8.05 (d, J=8 Hz, 2H), 7.67 (d, J=8 Hz, 2H), 6.27 (s, 1H), 3.62 (s, 2H), 3.32 (s, 3H), 2.07-1.83 (m, 2H), 1.14 (s, 9H).

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
  5. customby recrystallization with DCM/hexanes

Sources & evidence

ORD record
ord-238c9e5f134b4b61a8fe5ab241852035
Source dataset
uspto-grants-2015_08
Patent number
US09096532B2

Reaction notes

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