Tetrahydrofuran → HCID 66765443, compound

To a solution of 3-(dimethylamino)propane-1,2-diol (934 mg, 7.84 mmol) in CH2Cl2 (8 mL) were added Bu2SnO (42 mg, 0.16 mmol), tosyl chloride (1.49 g, 7.84 mmol), and Et3N (1.10 mL, 7.92 mmol). The reaction mixture was stirred at rt for 2 hrs. The mixture was quenched with water (30 mL) and extracted with EtOAc (two×30 mL). The combined organic layers were dried over MgSO4 and concentrated to afford 3-dimethylamino-2-hydroxypropyl 4-methylbenzenesulfonate; [m/z (APCI+) 274.10 (M+H)+]. The residue was dissolved in THF (10 mL), then DBU (2.56 mL, 16.6 mmol) and 4-nitro-1H-pyrazole (602 mg, 5.32 mmol) were added and the resulting mixture was stirred at rt for 30 min. The mixture was then quenched with water (30 mL) and extracted with EtOAc (two×30 mL). The combined organic layer were dried over MgSO4 and concentrated to give the title compound as a pale yellow oil (526 mg, 46° A yield) which was used without purification. m/z (APCI+) for C8H14N4O3 215.10 (M+H)+.

1. customThe mixture was then quenched with water (30 mL)
2. extractionextracted with EtOAc (two×30 mL)
3. dry with materialThe combined organic layer were dried over MgSO4
4. concentrationconcentrated

ORD record

ord-9e6c63ee36f94e2190858c3595641ba4

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040547B2