5-(1-benzyl-2-(pyridin-3-yl)-1H-imidazol-5-yl)-4-methyl-2-phenylthiazole → 4-methyl-2-phenyl-5-(2-(pyridin-3-yl)-1H-imidazol-5-yl)thiazole

HRID 2274516Notes

Reaction equation

HRID 2274516 reaction equation
C([N:8]1[C:12]([C:13]2[S:17][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:15][C:14]=2[CH3:24])=[CH:11][N:10]=[C:9]1[C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)C1C=CC=CC=1.[H][H]>CO>[CH3:24][C:14]1[N:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[S:17][C:13]=1[C:12]1[NH:8][C:9]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)=[N:10][CH:11]=1

Participants

4

Reactant 2

HCID 592524745-(1-benzyl-2-(pyridin-3-yl)-1H-imidazol-5-yl)-4-methyl-2-phenylthiazole2×HCID 178418361HCID 178418361, compound

Product 1

HCID 592524564-methyl-2-phenyl-5-(2-(pyridin-3-yl)-1H-imidazol-5-yl)thiazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound is prepared from 5-(1-benzyl-2-(pyridin-3-yl)-1H-imidazol-5-yl)-4-methyl-2-phenylthiazole (Example 71) in a similar manner as described in Tetrahedron Letters, 2008, 64(26), 6060-6072. In this case, 5-(1-benzyl-2-(pyridin-3-yl)-1H-imidazol-5-yl)-4-methyl-2-phenylthiazole in methanol is debenzylated by hydrogenation under an atmospheric pressure of hydrogen using a balloon with vigorous stirring for 70 h under reflux. The reaction mixture is filtered through Celite, filtered and concentrated under reduced pressure. The residue is chromatographed on silica to give the title compound.

Workup

  1. temperatureunder reflux
  2. filtrationThe reaction mixture is filtered through Celite
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is chromatographed on silica

Sources & evidence

ORD record
ord-d7cf63b5eeb94dec890fa9ee8095f653
Source dataset
uspto-grants-2015_09
Patent number
US09126973B2

Reaction notes

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