HCID 67070204, compound → HCID 67070018, compound

HRID 2390813Notes

Reaction equation

HRID 2390813 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[C:9]([O:14][CH3:15])=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][C:5]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:4][C:3]=1[C:20]#[C:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])=[CH:24][CH:23]=1.[H][H]>CCOC(C)=O.CO.[OH-].[OH-].[Pd+2]>[NH2:1][C:2]1[C:7]([C:8]2[C:9]([O:14][CH3:15])=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][C:5]([C:16]([CH3:17])([CH3:18])[CH3:19])=[CH:4][C:3]=1[CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])=[CH:26][CH:27]=1

Participants

6

Reactant 2

HCID 67070204HCID 67070204, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67070018HCID 67070018, compoundYield 70.7%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

step 4—A mixture of 84 (0.131 g, 0.29 mmol) and Pd(OH)2 (20% wt. on carbon, 0.100 g) in EtOAc (20 mL) and MeOH (20 mL) in a Parr bottle at RT was shaken under 40 psi hydrogen atmosphere for 45 min. The catalyst was filtered and the filtrate was concentrated to afford 0.093 g (66%) of N-(4-{2-[2-amino-5-tert-butyl-3-(2-methoxy-pyridin-3-yl)-phenyl]-ethyl}-phenyl)-methanesulfonamide (86) as an off-white solid.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-66151714223f44cc848b7f42655d3484
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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