HCID 57961674, compound → tert-Butyl (3-{[(3-aminobenzoyl)amino]methyl}phenyl)carbamate

To a solution tert-butyl (3-[{(3-nitrobenzoyl)amino]methyl}phenyl)carbamate (1.50 g, 4.04 mmol) in water (2.91 mL), methanol (16 mL) and acetic acid (6.2 mL) was added iron (0.564 g, 10.1 mmol) powder in small quantities. When the addition was completed, the mixture was stirred in water bath for 4 h, and the reaction was complete. The mixture was filtered, and the cake was washed with MeOH/EtOAc. The brown filtrate was concentrated and diluted with H2O, and the aqueous layer was extracted with EtOAc three times. The combined organic layers were dried, filtered and concentrated to give the desired product as a brown solid (1.8 g). LCMS for C19H23N3O3 (M+H)+: m/z=342.1. 1H NMR (400 MHz, CD3OD): δ 7.38 (t, J=2.0 Hz, 1H), 7.28 (ddd, J=8.0, 2.0, 1.2 Hz, 1H), 7.22 (t, J=8.0 Hz, 1H), 7.16 (s, 1H), 7.14 (t, J=8.0 Hz, 1H), 7.08 (m, 1H), 6.96 (ddd, J=8.0, 2.4, 1.2 Hz, 1H), 6.85 (ddd, J=8.0, 2.0, 1.2, 1H), 4.50 (s, 2H), 1.50 (s, 9H).

1. additionWhen the addition
2. filtrationThe mixture was filtered
3. washthe cake was washed with MeOH/EtOAc
4. concentrationThe brown filtrate was concentrated
5. additiondiluted with H2O
6. extractionthe aqueous layer was extracted with EtOAc three times
7. customThe combined organic layers were dried
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-838975b104ee448ba61011c7c12ee6fb

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871753B2