Diisopropylethylamine → tert-butyl N-[N-(5-propan-2-yl-1-quinolin-6-ylpyrazole-4-carbonyl)carbamimidoyl]carbamate

To a solution of 5-isopropyl-1-(6-quinolinyl)-1H-pyrazole-4-carboxylic acid (336.7 mg, 1.2 mmol) in 5 ml dimethylformamide was added N,N-diisopropylethylamine (0.42 ml, 2.39 mmol), benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent) (582 mg, 1.32 mmol) and tert-butoxycarbonylguanidine (210 mg, 1.32 mmol). The resulting solution was stirred at room temperature for 2 h, then heated to 60° C. for 2 h. The reaction mixture was then cooled to room temperature and concentrated to dryness in vacuo. The solid residue was partitioned between ethyl acetate and water. The ethyl acetate layer was washed with brine, dried (sodium sulfate) and concentrated to dryness in vacuo. The solid residue was triturated with methanol (1.5 ml), filtered, washed with diethyl ether and dried to yield the title compound as a white solid (114.3 mg, 22.5% yield).

1. temperatureheated to 60° C. for 2 h
2. temperatureThe reaction mixture was then cooled to room temperature
3. concentrationconcentrated to dryness in vacuo
4. customThe solid residue was partitioned between ethyl acetate and water
5. washThe ethyl acetate layer was washed with brine
6. dry with materialdried (sodium sulfate)
7. concentrationconcentrated to dryness in vacuo
8. customThe solid residue was triturated with methanol (1.5 ml)
9. filtrationfiltered
10. washwashed with diethyl ether
11. customdried

ORD-Eintrag

ord-9fcc380d12e54b589c47d7110a0a176e

Quelldatensatz

uspto-grants-2005_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06974813B2