Hydrochloric Acid → HCID 87740010, compound

Temperature

0 °C

A mixture of Example 45C (0.56 g, 2.1 mmol) in CHCl3 (4.2 mL) was treated with POCl3 (0.97 mL, 10.5 mmol), cooled to 0° C., treated with triethylamine (0.59 mL, 4.2 mmol), stirred at ambient temperature for 4 hours, diluted with CHCl3 (5 mL), treated with a stream of HCl gas for 2 minutes, stirred at ambient temperature overnight and partitioned between cold 1 M NaOH (50 mL) and CH2Cl2 (50 mL). The layers were separated and the aqueous was extracted with CH2Cl2 (2×50 mL). The combined CH2Cl2 layers were dried (MgSO4), filtered, concentrated under reduced pressure and chromatographed eluting with CH2Cl2 and then 9:1 CH2Cl2:EtOAc to provide the title compound. 1H NMR (DMSO-d6) δ 2.87 (t, J=5.76 Hz, 2H) 4.43 (t, J=5.93 Hz, 2H) 7.12 (s, 2H) 7.15 (d, J=8.81 Hz, 1H) 7.52 (dd, J=8.65, 2.88 Hz, 1H) 7.88 (d, J=2.71 Hz, 1H); MS (M+H)+ m/z 282.

1. stirringstirred at ambient temperature overnight
2. custompartitioned between cold 1 M NaOH (50 mL) and CH2Cl2 (50 mL)
3. customThe layers were separated
4. extractionthe aqueous was extracted with CH2Cl2 (2×50 mL)
5. dry with materialThe combined CH2Cl2 layers were dried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customchromatographed
9. washeluting with CH2Cl2

ORD record

ord-f8721110281047f989172dcec334d032

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08735411B2