Water → 4-[2-Amino-4-(3,5-dimethylphenyl)-1,3-thiazol-5-yl]-N-benzylpyridin-2-amine

HRID 1178592Notes

Reaction equation

HRID 1178592 reaction equation
[H-].[Li+].[Al+3].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[NH2:11][C:12]1[S:13][C:14]([C:25]2[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C:32](=O)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:26]=2)=[C:15]([C:17]2[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[CH:18]=2)[N:16]=1.O>O1CCCC1>[NH2:11][C:12]1[S:13][C:14]([C:25]2[CH:30]=[CH:29][N:28]=[C:27]([NH:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:26]=2)=[C:15]([C:17]2[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[CH:18]=2)[N:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 9952828N-[4-[2-AMINO-4-(3,5-DIMETHYLPHENYL)-1,3-THIAZOL-5-YL]-2-PYRIDYL]BENZAMIDEHCID 21226445Aluminium lithium hydride

Product 1

HCID 219641944-[2-Amino-4-(3,5-dimethylphenyl)-1,3-thiazol-5-yl]-N-benzylpyridin-2-amineYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Aluminum lithium hydride (0.16 g, 4.1 mmol) was added to a suspension of aluminum chloride (0.55 g, 4.1 mmol) in anhydrous tetrahydrofuran (30 mL) and the mixture was stirred at room temperature for 15 minutes. A solution of N-[4-[2-amino-4-(3,5-dimethylphenyl)-1,3-thiazol-5-yl]-2-pyridyl]benzamide (0.40 g, 1.0 mmol) in anhydrous tetrahydrofuran (10 mL) was added to the mixture and the resulting mixture was heated to reflux for 2 hours. After the reaction mixture was cooled to room temperature, water was added and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated. The residue was recrystallized from ethyl acetate-hexane to obtain 0.20 g (0.51 mmol, yield 51%) of the title compound.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperatureAfter the reaction mixture was cooled to room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-faf972d76c814222b489366d9ee6c76f
Source dataset
uspto-grants-2007_10
Patent number
US07276527B2

Reaction notes

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