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

HRID 1521587Notes

Reaction equation

HRID 1521587 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-9283901c61504edb88e86428fc797b49
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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