1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (S)-N-(6-Fluoropyridin-3-yl)-2-methylpyrrolidine-2-carboxamide
Reaktionsgleichung
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@@:9]1([CH3:16])[C:13]([OH:15])=O)=O)(C)(C)C.[F:17][C:18]1[N:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C>CN1CCCC1=O>[F:17][C:18]1[N:23]=[CH:22][C:21]([NH:24][C:13]([C@:9]2([CH3:16])[CH2:10][CH2:11][CH2:12][NH:8]2)=[O:15])=[CH:20][CH:19]=1Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 65 °C
Versuchsvorschrift
To a stirred solution of (5)-1-(tert-butoxycarbonyl)-2-methylpyrrolidine-2-carboxylic acid (1.0 g, 4.37 mmol) and 6-fluoropyridin-3-amine (1.47 g, 13.1 mmol), 1-hydroxybenzotriazole (0.65 mg, 4.81 mmol), and N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide (2.5 g, 13.1 mmol) in N-methylpyrrolidinone (10 mL) was added diisopropylethylamine (3.8 mL, 21.8 mmol). The reaction mixture was heated to 65° C. for 12 h and the solvent was evaporated to dryness. The residue was separated by preparative HPLC. The crude product was dissolved in methanol and 4N HCl in dioxane (4 mL) was added. The reaction mixture was stirred at room temperature overnight and the crude product was used in the next step without further purification. LC/MS [M+H]+: 224; Ret time (Method F): 0.78 min.
Aufarbeitung
- customthe solvent was evaporated to dryness
- customThe residue was separated by preparative HPLC
- dissolutionThe crude product was dissolved in methanol
- addition4N HCl in dioxane (4 mL) was added
- customthe crude product was used in the next step without further purification
- custom0.78 min.
Quellen und Nachweise
- ORD-Eintrag
- ord-0e5787db47444ff19c26f8631e4f81a0
- Quelldatensatz
- uspto-grants-2013_04
- Patentnummer
- US08415340B2
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