Benzoic Acid → HCID 44199933, compound

Temperature

100 °C

To a solution of benzoic acid (0.67 g, 5.5 mmol), HATU (2.09 g, 11 mmol) and DIPEA (1.05 mL, 6 mmol) in dry DMF (10 mL) at rt in the presence of anhydrous Na2SO4 (7 g, 50 mmol) was added 17 (1.69 g, 5 mmol) slowly. The consumption of 17 was determined to be completed by LC/MS. Additional anhydrous DMF (40 mL) was added and the mixture was heated at 100° C. for 1 h. Solid was filtered off and most of DMF was removed under vacuum. The residue was partitioned between a mixture of water (150 mL), aqueous Na2CO3 (2 M, 10 mL), EtOAc (200 mL) and MeOH (20 mL). The organic phase was washed further with water (2×50 mL). After drying and removal of EtOAc, the solid residue was suspended and stirred in ACN (40 mL) for 16 h. Filtration and washing with copies amounts of ACN yielded A7 as a solid. 1H NMR (400 MHz, d4-MeOH) δ 9.03 (s, 1H), 8.12 (s, 1H), 8.1 (d, J=1.5 Hz, 1H), 8.05 (s, 1H), 7.83 (s, 1H), 7.65 (d, J=6.2 Hz, 1H), 7.59 (d, J=6.3 Hz, 1H), 7.57 (d, J=7.2 Hz, 1H), 7.5 (d, J=2.4 Hz, 1H), 7.43 (dd, J=8.3, 2.5 Hz, 1H), 7.27 (d, J=8.4 Hz, 1H), 3.84 (s, 3H), 2.83 (s, 3H), 2.18 (s, 3H). MS m/z 424.1 (M+1).

1. customThe consumption of 17
2. additionAdditional anhydrous DMF (40 mL) was added
3. filtrationSolid was filtered off and most of DMF
4. customwas removed under vacuum
5. customThe residue was partitioned between a mixture of water (150 mL), aqueous Na2CO3 (2 M, 10 mL), EtOAc (200 mL) and MeOH (20 mL)
6. washThe organic phase was washed further with water (2×50 mL)
7. customAfter drying
8. customremoval of EtOAc
9. filtrationFiltration
10. washwashing with copies amounts of ACN

ORD record

ord-2b0bdf986410460ea64649740135af3d

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278452B2