Diisopropylethylamine → HCID 44540783, Verbindung

A solution of 6-(4-morpholinylmethyl)-2-pyridinecarboxylic acid (33 mg, 0.15 mmol) in DMF (0.8 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). The mixture was stirred at room temperature for 15 mins then left to stand for 2 h. The reaction 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 (1 ml) and hydrochloric acid (2M, 0.080 ml) was added. After about 1 hour the solvent was evaporated under a stream of nitrogen 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 (11 mg) as a pale solid.

1. waitthen left
2. waitto stand for 2 h
3. extractionextracted with dichloromethane (3×10 ml)
4. customthe solvent was evaporated under nitrogen flow
5. dissolutionThe residue was dissolved in methanol (1 ml)
6. additionhydrochloric acid (2M, 0.080 ml) was added
7. customAfter about 1 hour the solvent was evaporated under a stream of nitrogen
8. customto give a crude product which
9. customwas purified by Mass Directed Automated Preparative HPLC (Method B)
10. additionFractions containing pure product
11. customwere evaporated under a nitrogen stream

ORD-Eintrag

ord-2ee5f6716bf04ebcb41e6ac7e11ed92e

Quelldatensatz

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08765743B2