Morpholine → HCID 90314992, compound

To a round-bottomed flask that had been purged with nitrogen, were added 3-bromopicolinic acid (500 mg, 2.50 mmol), morpholine (259 mg, 3.00 mmol), EDCI (712 mg, 3.70 mmol), HOBT (501 mg, 3.70 mmol), triethylamine (1.0 mL, 7.4 mmol) and DMF (12 mL). The mixture was stirred at rt for 24 h, before diluting with water (100 mL) and extracting with ethyl acetate (2×100 mL). The combined organic extracts were washed with saturated bicarbonate (1×50 mL), water (2×50 mL), dried with sodium sulfate, and concentrated to dryness. The crude product was purified by FCC to provide the title compound. MS (ESI): mass calcd. for C10H11BrN2O2, 270.00; m/z found, 271.0 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 8.57 (dd, J=4.7, 1.4, 1H), 7.93 (dd, J=8.2, 1.4, 1H), 7.23 (dd, J=8.2, 4.7, 1H), 3.90-3.77 (m, 4H), 3.74-3.62 (m, 2H), 3.30-3.15 (m, 2H).

1. customTo a round-bottomed flask that had been purged with nitrogen
2. extractionextracting with ethyl acetate (2×100 mL)
3. washThe combined organic extracts were washed with saturated bicarbonate (1×50 mL), water (2×50 mL)
4. dry with materialdried with sodium sulfate
5. concentrationconcentrated to dryness
6. customThe crude product was purified by FCC

ORD record

ord-09df04a463e54aaf88efa4553b267c4d

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09079866B2