Aluminium lithium hydride → 1-(4-fluorobenzyl)-4-(5-(hydroxymethyl)-4-methylthiazol-2-yl)-1H-1,2,4-triazol-5(4H)-one

HRID 554927

Reaktionsgleichung

Reaktionsgleichung von HRID 554927
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:11](=[O:12])[N:10]([C:13]3[S:14][C:15]([C:19](OCC)=[O:20])=[C:16]([CH3:18])[N:17]=3)[CH:9]=[N:8]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:11](=[O:12])[N:10]([C:13]3[S:14][C:15]([CH2:19][OH:20])=[C:16]([CH3:18])[N:17]=3)[CH:9]=[N:8]2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 57919964ethyl 2-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylate

Produkt 1

HCID 579199041-(4-fluorobenzyl)-4-(5-(hydroxymethyl)-4-methylthiazol-2-yl)-1H-1,2,4-triazol-5(4H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylate (2.26 g, 6.23 mmol) in anhydrous tetrahydrofuran (60.0 mL) was added lithium aluminium hydride (0.35 g, 9.33 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 4 h, then quenched with 10% aqueous hydrochloric acid solution (3 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was triturated with ether to the title compound: mp 164-166° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.64 (s, 1H), 7.30 (dd, J=8.7, 8.7 Hz, 2H), 7.15 (dd, J=8.7, 8.7 Hz, 2H), 4.96 (s, 2H), 4.57 (s, 2H), 2.22 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 163.7, 160.5, 150.2 (d, 3JC-F=12 Hz), 143.2, 132.8 (d, 3JC-F=11 Hz), 132.5, 130.7, 130.4 (d, 3JC-F=33 Hz), 116.9 (d, 3JC-F=86 Hz), 55.3, 48.1, 15.1; MS (ES+) m/z 321.2 (M+1).

Aufarbeitung

  1. customquenched with 10% aqueous hydrochloric acid solution (3 mL)
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was triturated with ether to the title compound

Quellen und Nachweise

ORD-Eintrag
ord-f52a525c868d49ec8b838341a5a01204
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08049016B2

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