Triethylamine → N-[4-[2-AMINO-4-(3,5-DIMETHYLPHENYL)-1,3-THIAZOL-5-YL]-2-PYRIDYL]BENZAMIDE

HRID 2212348Notes

Reaction equation

HRID 2212348 reaction equation
BrBr.[C:3]([NH:11][C:12]1[CH:17]=[C:16]([CH2:18][C:19]([C:21]2[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[CH:22]=2)=O)[CH:15]=[CH:14][N:13]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:29][C:30]([NH2:32])=[S:31].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C(O)(=O)C>[NH2:32][C:30]1[S:31][C:18]([C:16]2[CH:15]=[CH:14][N:13]=[C:12]([NH:11][C:3](=[O:10])[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:17]=2)=[C:19]([C:21]2[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[CH:22]=2)[N:29]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 24408BromineHCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 21964214HCID 21964214, compound

Product 1

HCID 9952828N-[4-[2-AMINO-4-(3,5-DIMETHYLPHENYL)-1,3-THIAZOL-5-YL]-2-PYRIDYL]BENZAMIDEYield 68.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (1.0 mL, 19 mmol) was added to a solution of 2-(2-benzoylamino-4-pyridyl)-1-(3,5-dimethylphenyl)ethanone (6.4 g, 19 mmol) in acetic acid (80 mL) at 0° C. and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated. The residue was dissolved in acetonitrile (100 mL), to the solution were added thiourea (1.5 g, 19 mmol) and triethylamine (2.8 mL, 20 mmol) and the mixture was stirred at 80° C. for 3 hours. After the reaction mixture was cooled to room temperature, a saturated aqueous solution of sodium hydrogencarbonate (200 mL) was added and the resulting solid was collected by filtration and washed with water. The resulting crude crystals were collected by filtration and washed with water. The crude crystals were recrystallized from ethanol to obtain 5.0 g (13 mmol, yield 68%) of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in acetonitrile (100 mL), to the solution
  3. stirringthe mixture was stirred at 80° C. for 3 hours
  4. temperatureAfter the reaction mixture was cooled to room temperature
  5. filtrationthe resulting solid was collected by filtration
  6. washwashed with water
  7. filtrationThe resulting crude crystals were collected by filtration
  8. washwashed with water
  9. customThe crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-e2be8d0ed7df415cb4afe98b5adc8977
Source dataset
uspto-grants-2006_09
Patent number
US07101899B1

Reaction notes

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