Reaktion #2161283

Reaktionsgleichung

4-(5-(4-fluorobenzyl)-1-(azetidin-3-yl)-1H-pyrazol-3-yl)pyridine

imidazole-2-carboxylic acid

HOBt

EDCI

NMM

→

title compound

4-{5-(4-fluorobenzyl)-1-[1-(1H-imidazol-2-ylcarbonyl)azetidin-3-yl]-1H-pyrazol-3-yl}pyridine

Lösungsmittel

Ether

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe volatiles were removed in vacuo
2. 2
   Sonstigethe residue purified directly by Biotage flash chromatography
3. 3
   Wascheneluting with 2-6% MeOH/DCM
4. 4
   Sonstigeto yield a clear gum
5. 5
   Sonstigethe mix sonicated
6. 6
   Sonstigeto give a white precipitate that
7. 7
   Filtrationwas filtered off
8. 8
   Waschenwashed with ether
9. 9
   Sonstigedried in-vacuo

Vorschrift

To a suspension of 4-(5-(4-fluorobenzyl)-1-(azetidin-3-yl)-1H-pyrazol-3-yl)pyridine (85 mg, 0.28 mmol) in DMF (3 mL) was added HOBt (45 mg, 0.33 mmol), EDCI (64 mg, 0.33 mmol), NMM (76 μL, 0.69 mmol) followed by imidazole-2-carboxylic acid (34 mg, 0.30 mmol) and the mixture stirred for 16 hours at room temperature. The volatiles were removed in vacuo and the residue purified directly by Biotage flash chromatography, eluting with 2-6% MeOH/DCM to yield a clear gum. Ether was added (5 mL) and the mix sonicated to give a white precipitate that was filtered off, washed with ether and dried in-vacuo to yield the title compound as a white solid, 78 mg, 70%. 1H NMR (400 MHz, DMSO-D6) δ ppm 13.04-13.12 (m, 1 H), 8.54 (d, 2 H), 7.74 (d, 2 H), 7.25-7.32 (m, 2 H), 7.18 (t, 2 H), 7.03-7.12 (m, 1 H), 6.66 (s, 1 H), 5.33-5.46 (m, 1 H), 4.77-4.92 (m, 2 H), 4.26-4.36 (m, 2 H), 4.12 (s, 2 H); m/z (APCI+) for C22H19N6FO 403.1 (M+H)+.

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