Diisopropylethylamine → HCID 25094826, Verbindung

BOP (11 g, 24 mmol) is added to a slurry of pyrazolo[1,5-a]pyridine-2,4-dicarboxylic acid 2-ethyl ester (5.6 g, 24 mmol), adamantan-1-ylmethylamine (4.4 g, 27 mmol), iPr2NEt (21 mL, 120 mmol), and DMF (240 mL) under N2. The reaction vessel is sealed and the mixture is left to stir for 15 h. EtOAc (200 mL) is added. The solution is washed with 50% sat. aq. NH4Cl (2×500 mL). The aqueous phases are extracted with EtOAc (3×200 mL). The combined organics are dried over Na2SO4, filtered, and concentrated. Purification by flash column chromatography (2:1 hexanes:EtOAc to 1:1 hexanes:EtOAc) affords the title compound as a tan solid. 1H NMR (400 MHz, CDCl3) δ: 8.62 (d, 1H), 7.60 (d, 1H), 7.44 (s, 1H), 7.00 (t, 1H), 6.23 (bs, 1H), 4.48 (q, 2H), 3.23 (d, 2H), 1.98-2.07 (m, 3H), 1.57-1.78 (m, 12H), 1.45 (t, 3H). LC-MS m/z (M+H+): 382.2; RT=1.09 min.

1. customThe reaction vessel is sealed
2. waitthe mixture is left
3. washThe solution is washed with 50% sat. aq. NH4Cl (2×500 mL)
4. extractionThe aqueous phases are extracted with EtOAc (3×200 mL)
5. dry with materialThe combined organics are dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customPurification by flash column chromatography (2:1 hexanes:EtOAc to 1:1 hexanes:EtOAc)

ORD-Eintrag

ord-dbfc92be4c1a4389b0a9953b8d899807

Quelldatensatz

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08580812B2