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 42322Notes

Reaction equation

HRID 42322 reaction equation
C(S1C=C(C)NC1(C1N(C2C=NC=CC=2)C=NC=1)C1C=CC=CC=1)C1C=CC=CC=1.C([N:38]1[C:42]([C:43]2[S:47][C:46]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[N:45][C:44]=2[CH3:54])=[CH:41][N:40]=[C:39]1[C:55]1[CH:56]=[N:57][CH:58]=[CH:59][CH:60]=1)C1C=CC=CC=1.[H][H]>CO>[CH3:54][C:44]1[N:45]=[C:46]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[S:47][C:43]=1[C:42]1[NH:38][C:39]([C:55]2[CH:56]=[N:57][CH:58]=[CH:59][CH:60]=2)=[N:40][CH:41]=1

Participants

5

Reactant 3

HCID 592524745-(1-benzyl-2-(pyridin-3-yl)-1H-imidazol-5-yl)-4-methyl-2-phenylthiazoleHCID 178418361HCID 178418361, compoundHCID 178431986HCID 178431986, 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-67942bb4ecb64a5ca77b88627fb22f9c
Source dataset
uspto-grants-2013_09
Patent number
US08536185B2

Reaction notes

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