Aniline → 2-morpholin-4-ylmethyl-6-nitro-N-phenyl-benzamide

A solution of compound 6 (0.62 g, 2.3 mmol) in THF (50 mL) was treated with thionyl chloride (0.94 mL), stirred at room temperature for 4 h, and evaporated to dryness. The residue was dissolved in THF (50 mL) and treated with aniline (0.58 mL, 6.4 mmol) and diisopropylethylamine (1.12 mL, 6.4 mmol). The reaction mixture was stirred for 4 h, concentrated, dissolved in dichloromethane (50 mL), washed with saturated aqueous sodium bicarbonate (25 mL) and brine (25 mL), dried with sodium sulfate, and concentrated. The crude residue of compound 7 then was purified by flash chromatography (5% methanol in dichloromethane).

1. customevaporated to dryness
2. dissolutionThe residue was dissolved in THF (50 mL)
3. stirringThe reaction mixture was stirred for 4 h
4. concentrationconcentrated
5. dissolutiondissolved in dichloromethane (50 mL)
6. washwashed with saturated aqueous sodium bicarbonate (25 mL) and brine (25 mL)
7. dry with materialdried with sodium sulfate
8. concentrationconcentrated
9. customThe crude residue of compound 7 then was purified by flash chromatography (5% methanol in dichloromethane)

ORD-Eintrag

ord-50adf64c1f5b4905ad6c63d130076fb1

Quelldatensatz

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08207153B2