4-[(Methoxymethoxy)methyl]-2-nitro-3-thiophenesulfonamide → 2-Amino-4-[(methoxymethoxy)methyl]-3-thiophenesulfonamide

4-[(Methoxymethoxy)methyl]-2-nitrothiophene-3-sulfonamide (1.8 g, 6.4 mmol) was reacted with iron powder (1.43 g, 4 equivalents) in acetic acid (70 mL) at 50° C. for 7.5 hours then concentrated under reduced pressure. A slurry of the residue in 5% methanol/dichloromethane (60 mL) and water (6 mL) was filtered through silica gel (20 g) and further rinsed with 5% methanol/dichloromethane (300 mL). The filtrate was concentrated under reduced pressure and the residue purified by flash chromatography on silica gel using a Biotage-12s column eluting with 2.5:97.5 methanol: dichloromethane to give 2-amino -4-[(methoxymethoxy)methyl]thiophene-3-sulfonamide (1 g, 62%). 1H NMR (300 MHz, DMSO-d6) δ ppm 3.30 (s, 3H), 4.53 (s, 2H), 4.66 (s, 2H), 6.28 (s, 1H), 6.61 (s, 2H), 6.94 (s, 2H).

1. concentrationthen concentrated under reduced pressure
2. filtrationA slurry of the residue in 5% methanol/dichloromethane (60 mL) and water (6 mL) was filtered through silica gel (20 g)
3. washfurther rinsed with 5% methanol/dichloromethane (300 mL)
4. concentrationThe filtrate was concentrated under reduced pressure
5. customthe residue purified by flash chromatography on silica gel using a Biotage-12s column
6. washeluting with 2.5:97.5 methanol

ORD record

ord-4247dab690824e7e9947e4b6f90796e8

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07662958B2