Dimethyl Sulfoxide → 4-[2-(Cyclohexylmethyl-amino)-benzooxazol-6-yloxy]-pyridine-2-carbonitrile

To a solution of the methylsulfoxide (32 mg, 0.41 mmol, 6.0 eq) in 1 mL of methylene chloride was added oxalyl chloride (2M, 0.135 mL, 0.27 mmol, 4.0 eq) at −78° C. After 15 minutes, the 4-(2-(cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)pyridine-2-carboxamide (25 mg, 0.068 mmol, 1.0 eq) in 2 mL of methylene chloride was added to the reaction mixture. After being stirred at that temperature for 20 minutes, triethyl amine (83 mg, 0.83 mmol, 12 eq) was added to mixture. The reaction mixture was stirred at −78° C. for 2 hours, and then was quenched with aqueous ammonium chloride solution. The resulting mixture was extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with water (5 mL), brine (5 mL), then dried over MgSO4, filtered, and evaporated under reduced pressure to give crude product, which was purified by reverse phase prep HPLC to give the title compound. MH+=349.0.

1. stirringThe reaction mixture was stirred at −78° C. for 2 hours
2. customwas quenched with aqueous ammonium chloride solution
3. extractionThe resulting mixture was extracted with ethyl acetate (2×20 mL)
4. washThe combined organic layers were washed with water (5 mL), brine (5 mL)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. customevaporated under reduced pressure
8. customto give crude product, which
9. customwas purified by reverse phase prep HPLC

ORD record

ord-fbd5ed30ca9d46e493e77d39c393e159

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08710048B2