Trifluoroacetic acid → 5-chloro-2-methyl-3H,4H-pyrrolo[2,1-f][1,2,4]triazin-4-one

Temperature

85 °C

A mixture of 1-amino-3-chloro-1H-pyrrole-2-carboxylic acid methyl ester, hydrochloride salt (11.0 g, 52.1 mmol) and trifluoroacetic acid (6.0 mL, 77.9 mmol) in acetonitrile (230 mL) was heated at 85° C. overnight. The reaction mixture was concentrated and treated with fresh acetonitrile (200 mL) and triethylamine (22.0 mL, 157.8 mmol). The reaction mixture was heated at 85° C. overnight and concentrated to small volume and diluted with water (100 mL). The mixture was then stirred at rt for 20 min. The precipitate was collected, washed with water and dried to give the title compound as a brown solid (7.67 g, 80%): 1H NMR (CD3OD): δ 7.28 (s, 1H), 6.42 (s, 1H), 2.20 (s, 3H); MS (ESI+) 184.02, 186.10 (M++H).

1. concentrationThe reaction mixture was concentrated
2. temperatureThe reaction mixture was heated at 85° C. overnight
3. concentrationconcentrated to small volume
4. additiondiluted with water (100 mL)
5. customThe precipitate was collected
6. washwashed with water
7. customdried

ORD record

ord-0688be2c467148fd9c9a5ff41e7986b5

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07030118B2