Pyridine → HCID 67397745, compound

To a suspension of 2-{[4-(carboxymethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid resin (5.0 g) synthesized in Example 461-4 in dimethylformamide (20 mL) were added pyridine (1.2 ml) and 4 mol/L-hydrochloric acid-dioxane solution (2.3 ml) and the mixture was gently stirred at room temperature for 30 min. The resin was collected by filtration, and washed three times with dimethylformamide. To the resin were added dimethylformamide (20 mL), pyridine (0.75 ml) and 2-chloro-1,3-dimethylimidazolinium chloride (1.6 g), and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added heptylamine (1.4 ml), and the mixture was stirred at room temperature overnight. The resin was collected by filtration from the mixture, successively washed three times with dimethylformamide, once with water and methanol, three times with tetrahydrofuran, once with methanol, and finally three times with dichloromethane, and vacuum dried to give the title pale-yellow resin (5.2 g).

1. filtrationThe resin was collected by filtration
2. washwashed three times with dimethylformamide
3. additionTo the resin were added dimethylformamide (20 mL), pyridine (0.75 ml) and 2-chloro-1,3-dimethylimidazolinium chloride (1.6 g)
4. stirringthe mixture was stirred at room temperature for 30 min
5. additionTo the reaction mixture was added heptylamine (1.4 ml)
6. stirringthe mixture was stirred at room temperature overnight
7. filtrationThe resin was collected by filtration from the mixture
8. washsuccessively washed three times with dimethylformamide
9. dry with materialonce with water and methanol, three times with tetrahydrofuran, once with methanol, and finally three times with dichloromethane, and vacuum dried

ORD record

ord-6821e2729adf4f0c9b792986307bbb58

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08026370B2