HCID 118098687, compound → HCID 118098685, compound

HRID 708817Notes

Reaction equation

HRID 708817 reaction equation
[CH2:1]([S:3]([C:6]1[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][C:7]=1[CH2:8][N:9]([CH3:17])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:5])=[O:4])[CH3:2]>CO.CCOC(C)=O.[Pd]>[NH2:22][C:19]1[CH:20]=[CH:21][C:6]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])=[C:7]([CH:18]=1)[CH2:8][N:9]([CH3:17])[C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15]

Participants

5

Reactant 1

HCID 118098687HCID 118098687, compound

Product 1

HCID 118098685HCID 118098685, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3A (2.2 g, 6.14 mmol) in MeOH (50 ml) and EtOAc (50.0 ml) was added 10% Pd on carbon (0.653 g, 0.614 mmol) and the mixture was stirred under a hydrogen balloon for 2 h. Pd/C was removed by filtration. The filtrate was concentrated to give 3B that was used for next step without further purification. 1H NMR (400 MHz, CDCl3) δ ppm 7.75 (d, J=8.35 Hz, 1H) 6.58-6.67 (m, 1H) 6.52 (s, 1H) 4.78 (s, 2H) 3.04-3.13 (m, 2H) 2.94 (s, 3H) 1.45 (d, J=39.11 Hz, 9H) 1.26 (t, J=7.47 Hz, 3H).

Workup

  1. customPd/C was removed by filtration
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-dea930735ec04d44b41df2c598a09451
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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