Sodium Bicarbonate → 4-[2-(2-Chlorophenyl)-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-amine

HRID 1727355Notes

Reaction equation

HRID 1727355 reaction equation
Br.[NH2:2][C:3]1[CH:8]=[C:7]([CH:9](Br)[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=2)=O)[CH:6]=[CH:5][N:4]=1.[Cl:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([NH2:25])=[S:24].C(=O)([O-])O.[Na+]>CN(C)C=O>[Cl:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]1[S:24][C:9]([C:7]2[CH:6]=[CH:5][N:4]=[C:3]([NH2:2])[CH:8]=2)=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=2)[N:25]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27348242-ChlorothiobenzamideHCID 21964204HCID 21964204, compound

Product 1

HCID 219641924-[2-(2-Chlorophenyl)-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-amineYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(2-amino-4-pyridyl)-2-bromo-1-(3-methylphenyl)ethanone hydrobromide (5.00 g, 12.3 mmol) and 2-chlorothiobenzamide (1.06 g, 11.9 mmol) in N,N-dimethylformamide (40 mL) was stirred for 14 hours at room temperature. Aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and extracted with ethyl acetate. The extracts were washed with water, dried, and concentrated. The residue was purified by silica gel column chromatography (hexaneethyl acetate=4:1 to 2:1) to obtain a crystal. This crystal was washed with isopropyl ether, to obtain a title compound (3.15 g, yield 81%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexaneethyl acetate=4:1 to 2:1)
  6. customto obtain a crystal
  7. washThis crystal was washed with isopropyl ether

Sources & evidence

ORD record
ord-6c86dc2438184e89a4f1b8222efc6938
Source dataset
uspto-grants-2009_02
Patent number
US07495018B2

Reaction notes

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