Reaktion #45013

Reaktionsgleichung

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

methyl 4-pyrazol-1-ylbenzoate

AlMe3

→

N-[5-[2-(3-Methoxyphenyl)ethyl]-2H-pyrazol-3-yl]-4-pyrazol-1-yl-benzamide

Lösungsmittel

formic acid

toluene

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigequenched with damp sodium sulfite
2. 2
   workup.STIRRINGfurther stirred for 20 mins
3. 3
   Filtrationbefore being filtered
4. 4
   SonstigeThe solvent was removed in vacuo
5. 5
   Sonstigeto yield a yellow gum
6. 6
   SonstigeThe reaction mixture was evaporated to dryness
7. 7
   Wascheneluting initially with methanol
8. 8
   SonstigeAfter solvent removal
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 (155 mg, 55%)

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-pyrazol-1-ylbenzoate (177 mg, 0.88 mmol) and AlMe3 (0.93 ml, 1.8 mmol). The reaction mixture was stirred overnight. The reaction mixture was diluted with DCM (15 ml), quenched with damp sodium sulfite and further stirred for 20 mins before being filtered. The solvent was 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 mixture was evaporated to dryness and the resulting product was passed through a SCX column, eluting initially with methanol followed by 2N ammonia/methanol. After solvent removal, a yellow solid was obtained which was triturated with hot acetonitrile to afford a white solid. The solid was filtered and dried (155 mg, 55%); 1H NMR (400.132 MHz, DMSO) δ 2.92 (s, 4H), 3.74 (s, 3H), 6.48 (s, 1H), 6.60 (s, 1H), 6.77 (d, 1H), 6.84-6.82 (m, 2H), 7.20 (t, 1H), 7.81 (s, 1H), 7.96 (d, 2H), 8.14 (d, 2H), 8.63 (s, 1H), 10.69 (s, 1H), 12.18 (s, 1H); MS: m/z 388 (MH+).

Quelle