Reaktion #45011

Reaktionsgleichung

5-[2-(3-Methoxyphenyl)ethyl]-2-tert-butyl-pyrazol-3-amine

methyl 4-benzamidobenzoate

AlMe3

→

4-Benzamido-N-[5-[2-(3-methoxyphenyl)ethyl]-2H-pyrazol-3-yl]benzamide

Lösungsmittel

formic acid

toluene

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigequenched with damp sodium sulfite
2. 2
   workup.STIRRINGThe reaction mixture was stirred for 20 mins
3. 3
   Filtrationbefore being filtered
4. 4
   Sonstigethe solvent removed in vacuo
5. 5
   Sonstigeto yield a yellow gum
6. 6
   SonstigeThe reaction was evaporated to dryness
7. 7
   Wascheneluting initially with methanol
8. 8
   SonstigeAfter removal of the solvent
9. 9
   Sonstigea yellow solid was obtained which
10. 10
    Sonstigewas triturated with hot acetonitrile
11. 11
    Sonstigeto afford a white solid
12. 12
    FiltrationThe solid was filtered
13. 13
    Sonstigedried (66 mg, 21%)

Vorschrift

5-[2-(3-Methoxyphenyl)ethyl]-2-tert-butyl-pyrazol-3-amine (0.2 g, 0.73 mmol) was dissolved in toluene (10 ml) and to this was added methyl 4-benzamidobenzoate (200 mg, 0.80 mmol) and AlMe3 (0.93 ml, 1.8 mmol). The reaction was stirred overnight. The reaction was diluted with DCM (15 ml) and quenched with damp sodium sulfite. The reaction mixture was stirred for 20 mins before being filtered and the solvent removed in vacuo to yield a yellow gum. This gum was dissolved in formic acid (12 ml) and heated at 82° C. overnight. The reaction was evaporated to dryness and the resulting product was passed through a SCX column, eluting initially with methanol followed by 2N ammonia/methanol. After removal of the solvent, a yellow solid was obtained which was triturated with hot acetonitrile to afford a white solid. The solid was filtered and dried (66 mg, 21%); 1H NMR (400.132 MHz, DMSO) δ 2.91 (s, 4H), 3.74 (s, 3H), 6.46 (brs, 1H), 6.77 (d, 1H), 6.83 (s, 2H), 7.20 (t, 1H), 7.64-7.54 (m, 3H), 7.90 (d, 2H), 8.02-7.97 (m, 4H), 10.46 (s, 1H), 10.55 (s, 1H), 12.15 (s, 1H); MS: m/z 441 (MH+).

Quelle