Triethylamine → 4-Methyl-piperazine-1-carboxylic acid [2-((R)-indan-1-ylamino)-quinolin-6-yl]-amide

Temperatur

80 °C

(R)—N2-Indan-1-yl-quinoline-2,6-diamine (0.25 g, 0.9 mmol) was dissolved in tetrahydrofuran (10 mL) and triethylamine (0.138 mL, 1.0 mmol) was added. At 0° C. triphosgene (121 mg, 0.4 mmol) was added and the reaction mixture subsequently heated to 80° C. for 3 h. Upon cooling to ambient temperature triethylamine (0.138 mL, 1.0 mmol) and 1-methyl-piperazine (0.1 mL, 0.9 mmol) were added and the whole reaction mixture was stirred over night at 50° C. After evaporation of the solvent, the residue was taken up in water and extracted with ethyl acetate. The combined organic phases were dried on sodium sulfate, filtered and the filtrate was evaporated. The residue was taken up in a small amount of ethyl acetate, sonicated and kept over night in a refrigerator whereby a crystalline precipitate formed. The precipitate was isolated and dried on vacuum to yield the title compound (190 mg; 52%) as an off-white solid; MS: m/e=402.6 (M+H+).

1. additionwere added
2. customthe whole reaction mixture
3. customAfter evaporation of the solvent
4. extractionextracted with ethyl acetate
5. customThe combined organic phases were dried on sodium sulfate
6. filtrationfiltered
7. customthe filtrate was evaporated
8. customsonicated
9. waitkept over night in a refrigerator whereby
10. customa crystalline precipitate formed
11. customThe precipitate was isolated
12. customdried on vacuum

ORD-Eintrag

ord-23f348de158e452a97caf0523d661d98

Quelldatensatz

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08183380B2