HCID 68870935, compound → HCID 68875522, compound

HRID 1986347Notes

Reaction equation

HRID 1986347 reaction equation
[N+:1]([C:4]1[C:5]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:6][C:7]([O:10][C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:20])[CH3:19])[CH:14]=[CH:15][CH:16]=2)=[N:8][CH:9]=1)([O-])=O.[H][H]>CO.ClCCl.[Pd]>[NH2:1][C:4]1[C:5]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:6][C:7]([O:10][C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:20])[CH3:19])[CH:14]=[CH:15][CH:16]=2)=[N:8][CH:9]=1

Participants

6

Reactant 2

HCID 68870935HCID 68870935, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68875522HCID 68875522, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

The product of Step 5 (37.7 g, 103.5 mmol) in MeOH (350 mL) and dichloromethane (350 mL) was hydrogenated for overnight with a balloon of hydrogen gas in the presence of 10% palladium on carbon (3.5 g). After filtration of the catalyst through a pad of Celite, the filtrate was concentrated in vacuo to afford the title compound as a crude foam (˜35 g, quantitative). 1H NMR (400 MHz, MeOD) δ ppm 7.56 (s, 1H), 7.39-7.40 (m, 1H), 7.19-7.34 (m, 5H), 7.07-7.11 (m, 1H), 6.73 (dt, 1H, 1.8 Hz, 7.1 Hz), 6.48 (s, 1H), 3.32-3.34 (m, 3H), 2.12 (s, 3H). MS (ES+) m/e 335 [M+H]+.

Workup

  1. filtrationAfter filtration of the catalyst through a pad of Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f162f79fe7b8484381cdacd732ac3849
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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