반응 #45013

반응 방정식

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

용매

formic acid

toluene

DCM

반응 조건

후처리

1. 1
   기타quenched with damp sodium sulfite
2. 2
   workup.STIRRINGfurther stirred for 20 mins
3. 3
   여과before being filtered
4. 4
   기타The solvent was removed in vacuo
5. 5
   기타to yield a yellow gum
6. 6
   기타The reaction mixture was evaporated to dryness
7. 7
   세척eluting initially with methanol
8. 8
   기타After solvent removal
9. 9
   기타a yellow solid was obtained which
10. 10
    기타was triturated with hot acetonitrile
11. 11
    기타to afford a white solid
12. 12
    여과The solid was filtered
13. 13
    기타dried (155 mg, 55%)

실험 절차

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+).

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