Triethylamine → 2-Amino-4-(2-pyridyl)thiazol-5-yl 2-pyridyl ketone

HRID 1361877Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=O)[CH2:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=[O:10].BrBr.C(N(CC)CC)C.[NH2:27][C:28]([NH2:30])=[S:29].C(=O)([O-])O.[Na+]>C(O)(=O)C>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:9]([C:8]1[S:29][C:28]([NH2:30])=[N:27][C:7]=1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:10]

Participants

Conditions

Temperature: 80 °C

Procedure

1,3-Di(2-pyridyl)propane-1,3-dione (1.17 g, 5.15 mmol) was dissolved in acetic acid (20 mL), and bromine (856 mg, 5.35 mmol) was added thereto, followed by stirring at 80° C. for 1 hour. The reaction mixture was concentrated under reduced pressure, and the resulting residue was suspended in ethanol (30 mL), and triethylamine (0.750 mL, 5.38 mmol) and thiourea (416 mg, 5.47 mmol) were added thereto, followed by stirring under heating and reflux for 30 minutes. Aqueous saturated sodium hydrogencarbonate solution was added to the reaction mixture, followed by extraction with chloroform. The solvent was distilled away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (chloroform:methanol=9:1) to afford the entitled Compound 630 (739 mg, 51%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
stirringby stirring
temperatureunder heating
temperaturereflux for 30 minutes
extractionfollowed by extraction with chloroform
distillationThe solvent was distilled away under reduced pressure
customthe resulting residue was purified through silica gel column chromatography (chloroform:methanol=9:1)

Sources & evidence

ORD record: ord-b756ff4b5d4e4898a65002674cedb26d
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07880013B2

Reaction notes

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