Hydrochloric Acid → HCID 135752502, compound

Temperature

82 °C

A mixture of methyl 1-amino-5-chloro-1H-pyrrole-2-carboxylate hydrochloride (Example 13 A, 2.2 g, 9.8 mmol) and 4 N HCl in dioxane (6.0 mL, 24 mmol) in acetonitrile (90 mL) was placed in a sealed tube and heated at 82° C. overnight. The reaction mixture was concentrated and diluted with fresh acetonitrile (100 mL) and triethylamine (5 mL). The reaction mixture was heated at 85° C. overnight, concentrated to dryness and diluted with EtOAc to 150 mL. The EtOAc solution was washed with 1 N HCl, followed by saturated NaHCO3 solution and brine. The solution was dried over MgSO4 and concentrated to a solid. The solid was triturated with Et2O/hexane to give the title compound as a brown solid (1.15 g, 64%): 1H NMR (CDCl3) δ 6.99 (d, 1H, J=4.38 Hz), 6.42 (d, 1H, J=4.38 Hz), 2.40 (s, 3H); MS (ESI+) 183.98, 185.97 (M++H).

1. customwas placed in a sealed tube
2. concentrationThe reaction mixture was concentrated
3. additiondiluted with fresh acetonitrile (100 mL) and triethylamine (5 mL)
4. temperatureThe reaction mixture was heated at 85° C. overnight
5. concentrationconcentrated to dryness
6. additiondiluted with EtOAc to 150 mL
7. washThe EtOAc solution was washed with 1 N HCl
8. dry with materialThe solution was dried over MgSO4
9. concentrationconcentrated to a solid
10. customThe solid was triturated with Et2O/hexane

ORD record

ord-582a7c75d28b42b297df5ad9e7d29039

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07030118B2