Diisopropylethylamine → HCID 44540686, Verbindung

A solution of 6-[(dimethylamino)methyl]-2-pyridinecarboxylic acid (27 mg, 0.15 mmol) in DMF (0.0008 ml) was treated with O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (72 mg, 0.19 mmol) and DIPEA (0.052 ml). After 5 minutes the resulting solution was added to 6-(1H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (33 mg, 0.10 mmol). After stirring for 90 mins at room temperature the mixture was treated with saturated sodium bicarbonate solution (10 ml) and extracted with dichloromethane (3×10 ml). The extracts were passed through a hydrophobic frit, combined and the solvent was evaporated under nitrogen flow. The residue was dissolved in methanol (2 ml) and hydrochloric acid (2M, 0.080 ml) was added. The solvents were evaporated under nitrogen stream to give a crude product which was purified by Mass Directed Automated Preparative HPLC (Method B). Fractions containing pure product were evaporated under a nitrogen stream to give the title compound (22 mg) as a pale solid.

1. extractionextracted with dichloromethane (3×10 ml)
2. customthe solvent was evaporated under nitrogen flow
3. dissolutionThe residue was dissolved in methanol (2 ml)
4. additionhydrochloric acid (2M, 0.080 ml) was added
5. customThe solvents were evaporated under nitrogen stream
6. customto give a crude product which
7. customwas purified by Mass Directed Automated Preparative HPLC (Method B)
8. additionFractions containing pure product
9. customwere evaporated under a nitrogen stream

ORD-Eintrag

ord-f0625fe98fe243f1a9901c7254e8246a

Quelldatensatz

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08765743B2