Ethanol → HCID 67419060, compound

Intermediate 102 (500 mg, 2.21 mmol) and (4-chlorophenyl)hydrazine hydrochloride (434 mg, 2.43 mmol) were dissolved in EtOH (10 mL) and AcOH (2 mL), and stirred for 18 h. The solvents were removed in vacuo and the residue was dissolved in DCM (50 mL) and washed with sat aq Na2CO3 (50 mL). The aqueous layer was extracted with DCM (50 mL) and the combined organic fractions were dried (MgSO4) and concentrated in vacuo. The residue was dissolved in DMF (10 mL) and Et3N (922 μL, 6.62 mmol) was added. The reaction mixture was heated using a microwave at 150° C. for 30 min. The solvents were removed in vacuo and the residue was purified by normal phase column chromatography to give the title compound as a white solid (137 mg, 20%). HRMS (ESI+) calcd for C16H15ClN4O, 315.1007. found 315.1011. HPLC (method B): Rf 4.45 min, 100% purity.

1. customThe solvents were removed in vacuo
2. dissolutionthe residue was dissolved in DCM (50 mL)
3. washwashed
4. extractionThe aqueous layer was extracted with DCM (50 mL)
5. dry with materialthe combined organic fractions were dried (MgSO4)
6. concentrationconcentrated in vacuo
7. dissolutionThe residue was dissolved in DMF (10 mL)
8. temperatureThe reaction mixture was heated
9. customat 150° C.
10. customfor 30 min
11. customThe solvents were removed in vacuo
12. customthe residue was purified by normal phase column chromatography

ORD record

ord-99d8fb692b034658a365c268dd5910d9

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09227967B2