4-Methylmorpholine → HCID 44156014, Verbindung

4-cyano-3-(3,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxylic acid (0.030 g, 0.07 mmol), HBTU (0.080 g, 0.21 mmol), N-methyl morpholine (0.023 mL, 0.21 mmol) and DMF (1 mL) were added to a sealed reaction tube containing 1,3-dimethyl-1H-pyrazol-5-amine (0.023 g, 0.21 mmol). The reaction mixture was allowed to shake overnight and was concentrated. The residue was dissolved up in THF/chloroform (1:3) (4 mL) and washed with sat NaHCO3 (2 mL). The organic solution was separated and concentrated. The crude product was dissolved in DMSO (1.5 mL) and was purified by reverse phase chromatography to give 4-cyano-3-(3,4-dichlorophenyl)-N-(1,3-dimethyl-1H-pyrazol-5-yl)-5-morpholin-4-ylthiophene-2-carboxamide (85) (0.003 g, 10%). LCMS: (FA) ES+ 476.4.

1. concentrationwas concentrated
2. dissolutionThe residue was dissolved up in THF/chloroform (1:3) (4 mL)
3. washwashed
4. customThe organic solution was separated
5. concentrationconcentrated
6. dissolutionThe crude product was dissolved in DMSO (1.5 mL)
7. customwas purified by reverse phase chromatography

ORD-Eintrag

ord-c81ab7cfe17847249b094d835e7dfec1

Quelldatensatz

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09029411B2