Reaktion #45153

Reaktionsgleichung

Hydrogen chloride

tert-butyl N-[1-[5-[[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]carbamoyl]pyrazin-2-yl]pyrrolidin-3-yl]-N-methylcarbamate

hydrogen chloride

→

title compound

Ausbeute 39.2%

N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]-5-(3-methylaminopyrrolidin-1-yl)pyrazine-2-carboxamide

Ausbeute 39.2%

Lösungsmittel

methanol

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe solution was stirred at room temperature for a further 16 h
2. 2
   Sonstigethe crude product was purified by ion exchange chromatography
3. 3
   WaschenThe desired product was eluted from the column
4. 4
   Sonstigewere evaporated to dryness
5. 5
   Sonstigeto afford impure product
6. 6
   SonstigeThe crude product was purified by preparative HPLC
7. 7
   workup.ADDITIONFractions containing the desired compound
8. 8
   Sonstigewere evaporated to dryness

Vorschrift

Hydrogen chloride (4M in dioxane, 0.57 mL, 2.26 mmol) was added to tert-butyl N-[1-[5-[[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]carbamoyl]pyrazin-2-yl]pyrrolidin-3-yl]-N-methylcarbamate (312 mg, 0.57 mmol) in methanol (2.80 mL) at 25° C. The resulting solution was stirred at room temperature for 48 h. The reaction was incomplete and further hydrogen chloride (4M in dioxane, 0.28 mL, 1.12 mmol) was added and the solution was stirred at room temperature for a further 16 h. The reaction mixture was diluted with MeOH (5 ml) and the crude product was purified by ion exchange chromatography, using a SCX column. The desired product was eluted from the column using 7M NH3/MeOH and fractions were evaporated to dryness to afford impure product. The crude product was purified by preparative HPLC, using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford the title compound (101 mg, 39%) as a white solid.

Quelle