Methyl 4-(1H-pyrazol-1-yl)benzoate → HCID 178490048, Verbindung

HRID 1911307Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1911307
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]2[CH:12]=[C:13]([NH2:20])[N:14](C(C)(C)C)[N:15]=2)[CH:6]=[CH:7][CH:8]=1.[N:21]1([C:26]2[CH:35]=[CH:34][C:29]([C:30](OC)=[O:31])=[CH:28][CH:27]=2)[CH:25]=[CH:24][CH:23]=[N:22]1.C[Al](C)C>C1(C)C=CC=CC=1.C(Cl)Cl.C(O)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]2[CH:12]=[C:13]([NH:20][C:30](=[O:31])[C:29]3[CH:28]=[CH:27][C:26]([N:21]4[CH:25]=[CH:24][CH:23]=[N:22]4)=[CH:35][CH:34]=3)[NH:14][N:15]=2)[CH:6]=[CH:7][CH:8]=1

Komponenten

7

Edukt 3

HCID 972639Methyl 4-(1H-pyrazol-1-yl)benzoateHCID 16682925TrimethylaluminumHCID 574539341-tert-butyl-3-(3-methoxyphenethyl)-1H-pyrazol-5-amine

Produkt 1

HCID 178490048HCID 178490048, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 284Formic AcidLösungsmittelHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
82 °C

Versuchsvorschrift

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+).

Aufarbeitung

  1. customquenched with damp sodium sulfite
  2. stirringfurther stirred for 20 mins
  3. filtrationbefore being filtered
  4. customThe solvent was removed in vacuo
  5. customto yield a yellow gum
  6. customThe reaction mixture was evaporated to dryness
  7. washeluting initially with methanol
  8. customAfter solvent removal
  9. customa yellow solid was obtained which
  10. customwas triturated with hot acetonitrile
  11. customto afford a white solid
  12. filtrationThe solid was filtered
  13. customdried (155 mg, 55%)

Quellen und Nachweise

ORD-Eintrag
ord-990f3525d2f74ed99a0b2ce11fa90938
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604022B2

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