Triethylamine → HCID 24954933, compound

To a solution of 3-chlorobenzaldehyde (0.16 ml, 1.4 mmol) in dichloromethane (10 ml) were added sequentially 2-aminoimidazole sulfate (0.19 g, 0.7 mmol), tetraisopropyl orthotitanate (0.51 ml, 1.7 mmol) and triethylamine (0.19 ml, 1.4 mmol). The reaction mixture was stirred at room temperature for 16 hours and then concentrated in vacuo. The residue was taken up in ethanol (5 ml) and then sodium borohydride (54 mg, 1.4 mmol) was added. The reaction mixture was stirred at room temperature for 3 hours and then quenched by the addition of water. After stirring for a further 15 minutes at room temperature, the reaction mixture was filtered and the filter cake washed with ethanol. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica gel (eluant:methanol/dichloromethane 0:100 to 10:90) to yield the title compound as an off-white solid (87 mg, 30%); MS (ISP): 208.7 ([M+H]+).

1. concentrationconcentrated in vacuo
2. stirringThe reaction mixture was stirred at room temperature for 3 hours
3. customquenched by the addition of water
4. stirringAfter stirring for a further 15 minutes at room temperature
5. filtrationthe reaction mixture was filtered
6. washthe filter cake washed with ethanol
7. concentrationThe filtrate was concentrated in vacuo
8. customthe residue was purified by chromatography on silica gel (eluant:methanol/dichloromethane 0:100 to 10:90)

ORD record

ord-5a2b9daeae4146c9ac114127c5ca6013

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07858653B2