Reaktion #45024

Reaktionsgleichung

5-Methoxycarbonylpyridine-2-carboxylic acid

DCM

tert-butyl 5-amino-3-[2-(3-methoxyphenyl)ethyl]pyrazole-1-carboxylate

chloride

→

desired product

Methyl 6-[[5-[2-(3-methoxyphenyl)ethyl]-2H-pyrazol-3-yl]carbamoyl]pyridine-3-carboxylate

Lösungsmittel

acetonitrile

formic acid

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was evaporated to dryness
2. 2
   Sonstigeto give
3. 3
   Sonstigeyield to a gum
4. 4
   workup.STIRRINGThe reaction mixture was stirred for 1 h
5. 5
   Sonstigebefore being evaporated to dryness
6. 6
   SonstigeThe resulting gum was quenched with saturated potassium carbonate (30 ml)
7. 7
   Extraktionextracted with DCM (3×50 ml)
8. 8
   Trocknendried (MgSO4)
9. 9
   Sonstigethe solvent removed in vacuo
10. 10
    Sonstigeto yield a viscous gum

Vorschrift

5-Methoxycarbonylpyridine-2-carboxylic acid (0.285 g, 1.58 mmol) was added to DCM (40 ml), to this was added oxayl chloride (0.165 ml, 1.90 mmol) and a few drops of anhydrous DMF. The reaction mixture was stirred for 30 mins before the addition of tert-butyl 5-amino-3-[2-(3-methoxyphenyl)ethyl]pyrazole-1-carboxylate (0.50 g, 1.58 mmol) and pyridine (2.0 ml). The reaction was stirred overnight. The reaction was evaporated to dryness to give yield to a gum. To this gum was added formic acid. The reaction mixture was stirred for 1 h before being evaporated to dryness. The resulting gum was quenched with saturated potassium carbonate (30 ml), extracted with DCM (3×50 ml), dried (MgSO4) and the solvent removed in vacuo to yield a viscous gum. Trituration with acetonitrile gave the desired product as a slightly yellow solid (24 mg, 4%); 1H NMR (400.132 MHz, DMSO) δ 2.92 (s, 4H), 3.74 (s, 3H), 3.95 (s, 3H), 6.50 (s, 1H), 6.76 (d, 1H), 6.83-6.82 (m, 2H), 7.20 (t, 1H), 8.26 (d, 1H), 8.53 (d, 1H), 9.17 (s, 1H), 10.38 (s, 1H), 12.31 (s, 1H); MH+381.

Quelle