Hydrochloric Acid → 2-Amino-3,3-dimethyl-N-(pyridin-2-yl)butanimidic acid

Temperature

120 °C

(S)-2-(tert-Butoxycarbonylamino)-3,3-dimethylbutanoic acid (1.00 g, 4.32 mmol), pyridine-2-amine (1.506 g, 16.00 mmol), DIEA (8.36 mL, 48 mmol), and HATU (7.87 g, 20.80 mmol) were taken up in ACN (5 mL) and heated at 120° C. for 30 minutes under microwave irradiation. ACN was removed under reduced pressure and the residue was dissolved in water and extracted with EtOAc (2×50 mL). The organic extracts were concentrated under reduced pressure and purified by preparative HPLC. Hydrogen chloride (4 M in THF, 4 mL, 16 mmol) was added to the resulting solid and the mixture was stirred at room temperature for 30 minutes. The solvent was removed under reduced pressure. The residue was dissolved in water and extracted with EtOAc (2×50 mL). The aqueous layer was basified with 30% NaOH solution. The resulting solid precipitate was removed by filtration. The filtrate was extracted with DCM (2×50 mL). The DCM layer was dried and concentrated to give the title compound (83 mg) as a brown liquid. LCMS m/z=208.2 [M+H]+.

1. customACN was removed under reduced pressure
2. dissolutionthe residue was dissolved in water
3. extractionextracted with EtOAc (2×50 mL)
4. concentrationThe organic extracts were concentrated under reduced pressure
5. custompurified by preparative HPLC
6. customThe solvent was removed under reduced pressure
7. dissolutionThe residue was dissolved in water
8. extractionextracted with EtOAc (2×50 mL)
9. customThe resulting solid precipitate was removed by filtration
10. extractionThe filtrate was extracted with DCM (2×50 mL)
11. dry with materialThe DCM layer was dried
12. concentrationconcentrated

ORD record

ord-4b91818559d0413d90ab175d5fd4e0f7

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778950B2