HCID 67309612, compound → HCID 67309424, compound

HRID 2383350Notes

Reaction equation

HRID 2383350 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:20]=[C:19]([C:21]#[N:22])[C:18]3[C:13](=[CH:14][C:15]([O:23]CC4C=CC=CC=4)=[CH:16][CH:17]=3)[CH:12]=2)=[N:8][C:7]=1[CH3:31])=[O:5])[CH3:2]>O1CCCC1.[C].[Pd]>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:20]=[C:19]([C:21]#[N:22])[C:18]3[C:13](=[CH:14][C:15]([OH:23])=[CH:16][CH:17]=3)[CH:12]=2)=[N:8][C:7]=1[CH3:31])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 67309612HCID 67309612, compound

Product 1

HCID 67309424HCID 67309424, compoundYield 31.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-(7-benzyloxy-4-cyanonaphthalene-2-yl)-4-methylthiazole-5-carboxylic acid ethyl ester (0.27 g) in tetrahydrofuran (20 mL) was added palladium-carbon (100 mg) at room temperature, and the mixture was stirred at the same temperature for 1.5 hours under a hydrogen atmosphere. The mixture was stirred at 50° C. overnight. The reaction mixture was filtered through a Celite pad, and the filtrate was concentrated under reduced pressure. The residue was suspended in ethyl acetate, and the resulting mixture was filtered. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=95/5-40/60) to give 2-(4-cyano-7-hydroxynaphthalene-2-yl)-4-methylthiazole-5-carboxylic acid ethyl ester (0.067 g). The title compound (0.019 g) was prepared by deprotecting this compound (0.030 g) in a similar manner to that described in Example 47.

Workup

  1. stirringThe mixture was stirred at 50° C. overnight
  2. filtrationThe reaction mixture was filtered through a Celite pad
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. filtrationthe resulting mixture was filtered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=95/5-40/60)

Sources & evidence

ORD record
ord-1cb4e299c8bc4e4d985e12d0eb62be45
Source dataset
uspto-grants-2012_09
Patent number
US08263622B2

Reaction notes

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