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

HRID 1882399ノート

反応式

HRID 1882399 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ee963080f70f45e4be41c9cec25e13e5
出典データセット
uspto-grants-2012_11
特許番号
US08318949B2

反応ノート

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