Ammonia → HCID 86687930, compound

4-Amino-N-(2-((tert-butyldimethylsilyl)oxy)ethyl)-5-chloro-2-methoxy-N-methylbenzamide (2.0 g, 5.3 mmol) was stirred in dichloromethane (100 mL) at −10° C. under an atmosphere of nitrogen and a 1M solution of boron trichloride in dichloromethane (10.68 mL, 10.7 mmol) was added dropwise. The reaction was allowed to warm to room temperature then left to stir at this temperature for 18 h. The reaction was cooled to −10° C. and a further 1 equivalent of boron trichloride solution was added dropwise, then the reaction was allowed to warm to room temperature and stirred for 3 h. After this time analysis by LCMS indicated that the reaction was complete. The reaction was cooled in a ice bath and methanol (20 mL) was added drop-wise to the reaction followed by 7N methanolic ammonia solution (17 mL) and then a further portion of MeOH (˜80 mL) until all the solids had dissolved. The solution was stirred for 1 h at room temperature then concentrated. The resulting residue was stirred with saturated aqueous NaHCO3 (150 mL) for 30 min then the aqueous phase was extracted with ethyl acetate. The combined extracts were washed with brine then passed through a phase separation cartridge and the solvent was removed under reduced pressure to afford a green gum (1.00 g, 77%). This material was taken through to the next step with no further purification.

1. waitthen left
2. temperatureThe reaction was cooled to −10° C.
3. temperatureto warm to room temperature
4. stirringstirred for 3 h
5. temperatureThe reaction was cooled in a ice bath
6. stirringThe solution was stirred for 1 h at room temperature
7. concentrationthen concentrated
8. stirringThe resulting residue was stirred with saturated aqueous NaHCO3 (150 mL) for 30 min
9. extractionthe aqueous phase was extracted with ethyl acetate
10. washThe combined extracts were washed with brine
11. customthen passed through a phase separation cartridge
12. customthe solvent was removed under reduced pressure

ORD record

ord-b3ba9348823242e08531c5cb6a1d5226

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796296B2