1-(1H-Imidazol-1-yl)ethanone → HCID 10320544, compound

HRID 1985093Notes

Reaction equation

HRID 1985093 reaction equation
[NH2:1][C@@H:2]([CH2:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[CH:22]=1)[C@H:3]([OH:19])[CH2:4][NH:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:16][CH3:17])[CH:14]=2)[N:9]([CH3:18])[CH2:8][CH2:7]1.[C:29](N1C=CN=C1)(=[O:31])[CH3:30]>ClCCl>[F:27][C:25]1[CH:26]=[C:21]([CH:22]=[C:23]([F:28])[CH:24]=1)[CH2:20][C@H:2]([NH:1][C:29](=[O:31])[CH3:30])[C@H:3]([OH:19])[CH2:4][NH:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:16][CH3:17])[CH:14]=2)[N:9]([CH3:18])[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 58909227HCID 58909227, compound

Product 1

HCID 10320544HCID 10320544, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(6-ethyl-1-methyl-1,2,3,4-tetrahydroquinolin-4-yl)amino]butan-2-ol (0.218 g) in dichloromethane (15 mL) was added 1-acetylimidazole (0.062 g). The mixture was stirred overnight at room temperature. The mixture was partitioned between dichloromethane and brine, and the organic was extracted three times, dried with sodium sulfate, filtered, and concentrated. A silica gel column was run for purification using 3% MeOH in dichloromethane with 0.5% NH4OH as the solvent solution. HPLC still showed small amounts of starting material present, so the mixture was washed one time with 1N HCl, dried with magnesium sulfate, filtered, and concentrated. 0.115 g of the title product were recovered. (48% yield). MS (ESI+) for C24H31F2N3O2 m/z 432.18 (M+H)+.

Workup

  1. customThe mixture was partitioned between dichloromethane and brine
  2. extractionthe organic was extracted three times
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customA silica gel column was run for purification
  7. washHPLC still showed small amounts of starting material present, so the mixture was washed one time with 1N HCl
  8. dry with materialdried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. custom0.115 g of the title product were recovered

Sources & evidence

ORD record
ord-70970de584bf481d8be67bbc1e605991
Source dataset
uspto-grants-2009_06
Patent number
US07544717B2

Reaction notes

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