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 (0.25 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 (0.25 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 record

ord-9e68906aacd14451a748d0073254ced9

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08779131B2