Ethylene carbonate → 2-[2-(4-Chloro-6-methoxy-pyridin-3-yl)-4-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-imidazol-1-yl]-ethanol

HRID 1530468ノート

反応式

HRID 1530468 の反応式
[Cl:1][C:2]1[C:7]([C:8]2[NH:9][CH:10]=[C:11]([C:13]3[N:14]([CH:19]([CH3:21])[CH3:20])[N:15]=[C:16]([CH3:18])[N:17]=3)[N:12]=2)=[CH:6][N:5]=[C:4]([O:22][CH3:23])[CH:3]=1.C1(=O)O[CH2:27][CH2:26][O:25]1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([O:22][CH3:23])[N:5]=[CH:6][C:7]=1[C:8]1[N:9]([CH2:27][CH2:26][OH:25])[CH:10]=[C:11]([C:13]2[N:14]([CH:19]([CH3:21])[CH3:20])[N:15]=[C:16]([CH3:18])[N:17]=2)[N:12]=1

参加物

4

反応物 2

HCID 7303Ethylene carbonateHCID 178491889HCID 178491889、化合物

生成物 1

HCID 582045242-[2-(4-Chloro-6-methoxy-pyridin-3-yl)-4-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-imidazol-1-yl]-ethanol収率 34%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
130 °C

実験手順

A suspension of 4-chloro-5-[4-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-1H-imidazol-2-yl]-2-methoxy-pyridine (5.9 g, 17.7 mmol) in toluene (20 mL) was treated with ethylene carbonate (50 mL) and heated at 130° C. for 2.5 h. The cooled reaction mixture was concentrated in vacuo then diluted with DCM and passed through a pad of silica eluting with DCM then 20% methanol in DCM. Methanolic fractions were combined and concentrated in vacuo and the resultant residue subjected to recrystallisation from acetonitrile to give the title compound as a pale tan solid (2.27 g, 34%). LCMS: RT=2.53 min [M+H]+ =377/379. 1H NMR 400 MHz (CDCl3) δ: 8.25 (1H, s), 8.05 (1H, s), 6.92 (1H, s), 5.82-5.80 (1H, m), 4.00 (3H, s), 3.97 (2H, t, J=4.92 Hz), 3.88 (2H, t, J=4.92 Hz), 2.38 (3H, s), 1.48 (6H, d, J=6.63 Hz).

後処理

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated in vacuo
  3. additionthen diluted with DCM
  4. concentrationconcentrated in vacuo
  5. customthe resultant residue subjected to recrystallisation from acetonitrile

出典と根拠

ORDレコード
ord-ad947268ccb1478c92ed0453c2e8708c
出典データセット
uspto-grants-2015_07
特許番号
US09090628B2

反応ノート

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