Salicylic Acid → HCID 18373206, compound

Temperature

0 °C

To a stirring solution of salicylic acid (1.06 g, 7.7 mmol) and DMF (1 drop) in dichloromethane (100 mL) at 0° C. was added oxalyl chloride (1.13 mL, mmol). After 1 h, the ice bath was removed and stirring was continued for 3.5 h. Solvent was removed under vacuum with minimum heat, and after evacuating further to remove residual oxalyl chloride, the residue was redissolved in dichloromethane (80 mL) and cooled to 0° C. To this solution was then added a solution of 1-Boc-6-aminoindazole (1.86 g, 8 mmol) in dichloromethane (10 mL). After stirring for 10 min, triethylamine (1.24 mL, 8 mmol) was added. After 1 h, the solution was transferred to a separatory funnel and washed with cold water (200 mL). The organic layer was then washed with cold satd aq NaHCO3 (200 mL), dried over MgSO4, filtered and concentrated under vacuum. The product was chromatographed over silica gel (0 to 60% EtOAc in hexane) and recrystallized from dichloromethane/hexanes to give 0.482 g (17%) of crystals.

1. customthe ice bath was removed
2. waitwas continued for 3.5 h
3. customSolvent was removed under vacuum with minimum heat
4. customafter evacuating further
5. customto remove residual oxalyl chloride
6. dissolutionthe residue was redissolved in dichloromethane (80 mL)
7. stirringAfter stirring for 10 min
8. waitAfter 1 h
9. customthe solution was transferred to a separatory funnel
10. washwashed with cold water (200 mL)
11. washThe organic layer was then washed with cold satd aq NaHCO3 (200 mL)
12. dry with materialdried over MgSO4
13. filtrationfiltered
14. concentrationconcentrated under vacuum
15. customThe product was chromatographed over silica gel (0 to 60% EtOAc in hexane)
16. customrecrystallized from dichloromethane/hexanes

ORD record

ord-22c7c55eb1e447d28da328844d605099

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06372759B1