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Sodium hydride → 12-Methoxy-4-(2-propan-2-yl-1,2,4-triazol-3-yl)-9-oxa-3,6,13-triazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene

HRID 1530473
ノート
印刷プレビュー

反応式

HRID 1530473 の反応式
Cl[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[N:5]=[CH:4][C:3]=1[C:10]1[N:11]([CH2:23][CH2:24][OH:25])[CH:12]=[C:13]([C:15]2[N:16]([CH:20]([CH3:22])[CH3:21])[N:17]=[CH:18][N:19]=2)[N:14]=1.[H-].[Na+]>CN(C=O)C>[CH:20]([N:16]1[C:15]([C:13]2[N:14]=[C:10]3[N:11]([CH2:23][CH2:24][O:25][C:2]4[CH:7]=[C:6]([O:8][CH3:9])[N:5]=[CH:4][C:3]=43)[CH:12]=2)=[N:19][CH:18]=[N:17]1)([CH3:22])[CH3:21]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 24758Sodium hydride2 回HCID 582047142-[2-(4-Chloro-6-methoxy-pyridin-3-yl)-4-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-imidazol-1-yl]-ethanol

生成物 1

HCID 5820487112-Methoxy-4-(2-propan-2-yl-1,2,4-triazol-3-yl)-9-oxa-3,6,13-triazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene収率 79.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

A solution of 2-[2-(4-chloro-6-methoxy-pyridin-3-yl)-4-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-imidazol-1-yl]-ethanol (7.52 g, 20.7 mmol) in DMF (100 mL) was cooled to 0° C. and treated with sodium hydride (804 mg, 20.1 mmol), the reaction mixture stirred at 0° C. for 10 min then allowed to warm to RT and stirred for 72 h. Further sodium hydride (150 mg) was added and stirring continued until no starting material remained before removal of solvent in vacuo. The residue was dissolved in ethyl acetate and the resultant solution washed three times with saturated brine then dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was triturated in pentane/diethyl ether (5:1) to give the title compound as a brown solid (5.38 g, 79%). LCMS RT=2.86, [M+H]+ =327. 1H NMR 400 MHz (CDCl3) δ: 9.35 (1H, s), 7.87 (1H, s), 7.63 (1H, s), 6.37 (1H, s), 6.03-6.02 (1H, m), 4.54-4.53 (2H, m), 4.53-4.33 (2H, m), 3.99 (3H, s), 1.57 (6H, d, J=6.63 Hz).

後処理

  1. temperatureto warm to RT
  2. stirringstirred for 72 h
  3. stirringstirring
  4. customremained before removal of solvent in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washthe resultant solution washed three times with saturated brine
  7. dry with materialthen dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe resultant residue was triturated in pentane/diethyl ether (5:1)

出典と根拠

ORDレコード
ord-c52341900e6c4aae89fb17d2effebf22
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09090628B2

反応ノート

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