Thionyl Chloride → 2-Chloro-N-[4-(2-furyl)-5-morpholinothiazol-2-yl]pyridine-4-carboxamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=O.S(Cl)(Cl)=O.[NH2:15][C:16]1[S:17][C:18]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[C:19]([C:21]2[O:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]([NH:15][C:16]2[S:17][C:18]([N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)=[C:19]([C:21]3[O:22][CH:23]=[CH:24][CH:25]=3)[N:20]=2)=[O:7])[CH:8]=[CH:9][N:10]=1Participants
Procedure
2-Chloroisonicotinic acid (5.00 g, 31.7 mmol) was added to thionyl chloride (40 mL), followed by stirring under heating and reflux for 2 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was dissolved in dichloromethane (1 mL). The resulting solution was added to a pyridine (16 mL) solution of 2-amino-4-(2-furyl)-5-morpholinothiazole (880 mg, 5.00 mmol) obtained in Step 1 of Example 29, and then N,N-dimethylaminopyridine (48.8 mmol, 0.400 mmol) was added thereto, followed by stirring at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:3 to ethyl acetate) to afford the entitled Compound 39 (1.05 g, 66%)
Workup
- temperatureunder heating
- temperaturereflux for 2 hours
- concentrationThe reaction mixture was concentrated under reduced pressure
- dissolutionthe resulting residue was dissolved in dichloromethane (1 mL)
- stirringby stirring at room temperature for 1 hour
- concentrationThe reaction mixture was concentrated under reduced pressure
- customthe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:3 to ethyl acetate)
Sources & evidence
- ORD record
- ord-158185b6cf154fba846b68b5752c0c0c
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08889718B2
Reaction notes
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