Furfurylamine → HCID 58856317, compound

A solution of 4-(dimethoxymethyl)benzoic acid 5 (2.94 g, 15 mmol), EDCI (5.75 g, 30 mmol), furfurylamine (3.5 mL, 37.5 mmol), and DMAP (122 mg, 1 mmol) in THF (200 mL) and CH2Cl2 (50 mL) was stirred at r.t. for 16 h. The solvent was removed by rotary evaporation and the resulting yellow oil was dissolved in CHCl3 and was washed twice with 0.5 M HCl. The organic solution was then vigorously stirred with 1.0 M HCl for 2 h. The layers were separated and the organic phase was washed twice more with 1.0 M HCl and once with brine. The organic phase was dried over Na2SO4 and the solvent was removed by rotary evaporation. The crude product was crystallized from hot EtOAc, yielding the title compound as a pale yellow solid in 2 crops (2.09 g, 58% yield). 1H NMR (400 MHz, CDCl3): δ 10.09 (s, 1H), 7.97 (s, 4H), 7.42 (m, 1H), 6.54 (br s, 1H), 6.39 (dd, J=2.0, 3.3 Hz, 1H), 6.35 (d, J=3.3 Hz, 1H), 4.69 (d, J=5.3 Hz, 2H).

1. customThe solvent was removed by rotary evaporation
2. dissolutionthe resulting yellow oil was dissolved in CHCl3
3. washwas washed twice with 0.5 M HCl
4. customThe layers were separated
5. washthe organic phase was washed twice more with 1.0 M HCl and once with brine
6. dry with materialThe organic phase was dried over Na2SO4
7. customthe solvent was removed by rotary evaporation
8. customThe crude product was crystallized from hot EtOAc

ORD record

ord-db7d3a5166574b57a09528df58584803

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07396936B1