Potassium Carbonate → HCID 53629629, compound

Temperature

160 °C

A mixture of 3-hydroxy-5-[(1S)-2-methoxy-(1-methylethyl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide (0.226 g, 0.74 mmol), methyl 5-chloropyrazine-2-carboxylate (192 mg, 1.11 mmol) and potassium carbonate (205 mg, 1.48 mmol) in acetonitrile (5 mL) was stirred in a ‘Biotage initiator Microwave’ at 160° C. for 4 hours. The solvent was removed in vacuo and water (30 mL) added. The mixture was acidified and extracted into ethyl acetate (3×50 mL), the combined organics washed with brine (30 mL), dried (MgSO4), filtered and reduced in vacuo to give a brown oil which was a mixture of the acid and methyl ester. Lithium hydroxide monohydrate (78 mg, 1.85 mmol) in water (2 mL) was added to the mixture of acid and ester (326 mg, 0.74 mmol) in THF (4 mL) and the mixture stirred at RT for 20 hours. The THF was removed in vacuo and the aqueous residue washed with ethyl acetate (20 mL) to remove impurities then acidified with 1M citric acid. The product was extracted into ethyl acetate (2×100 mL) and the combined organics washed with brine (50 mL), dried (MgSO4), filtered and reduced in vacuo to give a yellow solid (0.17 g). m/z 428 (M+H)+

1. customThe solvent was removed in vacuo and water (30 mL)
2. additionadded
3. extractionextracted into ethyl acetate (3×50 mL)
4. washthe combined organics washed with brine (30 mL)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. customto give a brown oil which
8. stirringthe mixture stirred at RT for 20 hours
9. customThe THF was removed in vacuo
10. washthe aqueous residue washed with ethyl acetate (20 mL)
11. customto remove impurities
12. extractionThe product was extracted into ethyl acetate (2×100 mL)
13. washthe combined organics washed with brine (50 mL)
14. dry with materialdried (MgSO4)
15. filtrationfiltered

ORD record

ord-e34f2bcd8b0942d6a76024073e46092e

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07842694B2