Cyclohexanol → 7-Bromo-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

HRID 1521587ノート

反応式

HRID 1521587 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=S)[CH2:6][CH2:5]2.[C:13]([NH:16][NH2:17])(=O)[CH3:14].C1(O)CCCCC1>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[C:13]([CH3:14])=[N:16][N:17]=[C:7]1[CH2:6][CH2:5]2

参加物

5

反応物 3

HCID 7966CyclohexanolHCID 14039AcetohydrazideHCID 573709906-Bromo-3,4-dihydroquinoline-2(1H)-thione

生成物 1

HCID 709778947-Bromo-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A flask containing the title compound from Example 22 Step A (100 mg, 0.413 mmol), acetic hydrazide (40.8 mg, 0.496 mmol) and cyclohexanol (2.00 ml, 0.413 mmol) was heated at reflux for 2 days. The reaction was then poured into water and extracted with ethyl acetate. The organic extracts were combined, washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel (0-15% methanol in ethyl acetate) provided the title compound: LCMS m/z 265.99 [M+2+H]+; 1H NMR (500 MHz, CDCl3) δ 7.53 (br s, 1H), 7.50 (d, J=8.57 Hz, 1H), 7.35 (d, J=8.57 Hz, 1H), 3.13-3.11 (m, 2H), 3.00-2.98 (m, 2H), 2.74 (s, 3H).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 2 days
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash chromatography on silica gel (0-15% methanol in ethyl acetate)

出典と根拠

ORDレコード
ord-9283901c61504edb88e86428fc797b49
出典データセット
uspto-grants-2015_07
特許番号
US09073929B2

反応ノート

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