Hexane → HCID 11545695, compound

Temperature

-78 °C

N-(2aminoethyl)morpholine (293 μL, 2.25 mmol) was dissolved in THF (7.5 mL) and was cooled down to −78° C. A 2.5N solution of nBuLi in hexane (1 mL, 2.5 mmol) was added dropwise. After 5 min. at −78° C., the mixture was stirred 1 h at −40° C. N-aryl-benzenesulfonamide building block XIII, e.g. 4-fluoro-N-(4-chlorophenyl)benzenesulfonamide (214 mg, 0.75 mmol), was added as a solid. The reaction mixture was stirred 2 h at room temperature, then overnight at 60° C. The reaction was quenched at room temperature with NH4Cl saturated solution in water (5 mL). The desired product was extracted with three portions of ethyl acetate (3×10 mL). Combined organic phases were dried over magnesium sulfate before filtering and removal of solvent. The crude product was purified by flash chromatography, using pure ethyl acetate as eluent. The desired product, e.g. N-(4-chlorophenyl)-4-{[2-(4-morpholinyl)ethyl]amino}benzenesulfonamide (184.2 mg, 62% yield) was obtained as a colorless oil, in 97% purity by BPLC (MaxPlot detection between 230 and 400 nm). This intermediate was used in the next step without further purification.

1. stirringThe reaction mixture was stirred 2 h at room temperature
2. customovernight
3. customat 60° C
4. customThe reaction was quenched at room temperature with NH4Cl saturated solution in water (5 mL)
5. extractionThe desired product was extracted with three portions of ethyl acetate (3×10 mL)
6. dry with materialCombined organic phases were dried over magnesium sulfate
7. filtrationbefore filtering
8. customremoval of solvent
9. customThe crude product was purified by flash chromatography

ORD record

ord-e5b5424638864fd480e37c6e77589c72

Source dataset

uspto-grants-2007_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07312358B2