Triethylamine → HCID 68089342, compound

To a solution of N6-methylquinoline-5,6-diamine (914 mg, 5.28 mmol) in DCM (30 mL) was added triethylamine (1.07 g, 10.57 mmol). A solution of methyl 4-chloro-3-methyl-4-oxobutanoate (1.3 g, 7.90 mmol) in DCM (10 mL) was added dropwise to the above solution over 5 min. The resulting mixture was stirred at room temperature for 20 min. The mixture was concentrated to dryness. To the residue was added acetic acid (10 mL). The solution was stirred at 60° C. for 2 h. The solvent was removed under reduce pressure and to the residue was added saturated sodium bicarbonate aqueous solution (20 mL). The mixture was extracted with DCM (3×40 mL). The combined organic layer was dried over sodium sulfate, filtered, and concentrated to dryness to give the crude product, which was purified by silica gel column chromatography (DCM/MeOH v/v 30:1) to give the title compound as a yellow solid (560 mg 33% yield). ESI MS: m/z 284.1 [M+H]+. 1H NMR (400 MHz, CDCl3): δ 8.94-8.88 (m, 2H), 7.95 (d, J=9.2 Hz, 1H), 7.71 (d, J=8.8 Hz, 1H), 7.50 (dd, J=4.4, 8.4 Hz, 1H), 3.94 (s, 3H), 3.70-3.63 (m, 4H), 3.28 (d, J=8.4 Hz, 0.5H), 3.23 (d, J=8.4 Hz, 0.5H), 2.86 (d, J=6.0 Hz, 0.5H), 2.82 (d, J=6.0 Hz, 0.5H), 1.47 (d, J=6.8 Hz, 3H).

1. concentrationThe mixture was concentrated to dryness
2. additionTo the residue was added acetic acid (10 mL)
3. stirringThe solution was stirred at 60° C. for 2 h
4. customThe solvent was removed
5. additionto the residue was added saturated sodium bicarbonate aqueous solution (20 mL)
6. extractionThe mixture was extracted with DCM (3×40 mL)
7. dry with materialThe combined organic layer was dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated to dryness
10. customto give the crude product, which
11. customwas purified by silica gel column chromatography (DCM/MeOH v/v 30:1)

ORD record

ord-273d4367ab214a35a936d85328f1eae2

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249162B2