Triethylamine → N-[4-[2-Amino-4-(4-methoxyphenyl)-1,3-thiazol-5-YL]-2-pyridyl]benzamide

HRID 2212347Notes

Reaction equation

HRID 2212347 reaction equation
BrBr.[C:3]([NH:11][C:12]1[CH:17]=[C:16]([CH2:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][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]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[N:29]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 24408BromineHCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 219642602-(2-Benzoylamino-4-pyridyl)-1-(4-methoxyphenyl)ethanone

Product 1

HCID 9865835N-[4-[2-Amino-4-(4-methoxyphenyl)-1,3-thiazol-5-YL]-2-pyridyl]benzamideYield 21%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (0.11 mL, 2.1 mmol) was added to a solution of 2-(2-benzoylamino-4-pyridyl)-1-(4-methoxyphenyl)ethanone (0.72 g, 2.1 mmol) in acetic acid (20 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 (20 mL), to the solution were added thiourea (0.17 g, 2.2 mmol) and triethylamine (0.35 mL, 2.5 mmol) and the mixture was stirred at 80° C. for 5 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 filtered 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 0.17 g (0.43 mmol, yield 21%) of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in acetonitrile (20 mL), to the solution
  3. stirringthe mixture was stirred at 80° C. for 5 hours
  4. temperatureAfter the reaction mixture was cooled to room temperature
  5. filtrationthe resulting solid was filtered
  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-af12d9ff3a184a6aa991a96e4955396e
Source dataset
uspto-grants-2006_09
Patent number
US07101899B1

Reaction notes

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