Acetic Acid → Methyl 2-(4-(pyridin-3-yl)benzylamino)thiazole-5-carboxylate

HRID 624227

Reaction equation

HRID 624227 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=2)[CH:2]=1.[NH2:15][C:16]1[S:17][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][N:20]=1.C(O)(=O)C.[BH4-].[Na+]>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:14]=[CH:13][C:10]([CH2:11][NH:15][C:16]3[S:17][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][N:20]=3)=[CH:9][CH:8]=2)[CH:2]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 238005Methyl 2-aminothiazole-5-carboxylateHCID 36930464-(Pyridin-3-yl)benzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 86665086Methyl 2-(4-(pyridin-3-yl)benzylamino)thiazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

In a 250 mL round-bottomed flask was added 4-(pyridin-3-yl)benzaldehyde (4 g, 21.83 mmol), methyl 2-aminothiazole-5-carboxylate (3.45 g, 21.83 mmol), and acetic acid (0.375 ml, 6.55 mmol) in toluene (109 ml). The mixture was heated at reflux under Dean-Stark conditions for 3 hours, cooled, concentrated and redissolved in methanol. The mixture was cooled to 0° C. and sodium borohydride (1.322 g, 34.9 mmol) was carefully added. The mixture was warmed to room temperature and the resulting suspension was filtered with water washes to provide the title compound after drying.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux under Dean-Stark conditions for 3 hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. dissolutionredissolved in methanol
  6. temperatureThe mixture was warmed to room temperature
  7. filtrationthe resulting suspension was filtered with water

Sources & evidence

ORD record
ord-cebf238a35b74ebcad8abec2965ad3a0
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Linked notes

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