Triethylamine → HCID 15481712, compound

HRID 1859007Notes

Reaction equation

HRID 1859007 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:24])([C@H:16]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.[CH2:25]([N:27](CC)CC)C.N#CBr>C(#N)C>[C:25]([N:21]1[CH2:20][CH2:19][N:18]([C@H:16]([CH3:17])[C@:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])([OH:24])[CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH2:23][CH2:22]1)#[N:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10476Cyanogen BromideHCID 15481711HCID 15481711, compound

Product 1

HCID 15481712HCID 15481712, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a cooled (0° C.) mixture of (2R,3R)-2-(2,4-difluorophenyl)-3-(piperazin-1-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 2 (250 mg, 0.74 mmol) and triethylamine (0.42 ml, 3 mmol) in acetonitrile (15 ml) was added cyanogen bromide (160 mg, 1.5 mmol) in acetonitrile (0.5 ml). The reaction mixture was stirred at room temperature for 18 h. The solvent was removed under reduced pressure. To the resulting residue water was added and extracted with ethyl acetate (3×20 ml). The combined organic extract was washed with water, brine and dried over magnesium sulphate. The solvent was removed and the product was purified on a column of silica gel (hexane/EtOAc, 1:1) to give the title compound as a colorless solid (150 mg, 56%).

Workup

  1. temperatureTo a cooled
  2. customThe solvent was removed under reduced pressure
  3. additionTo the resulting residue water was added
  4. extractionextracted with ethyl acetate (3×20 ml)
  5. extractionThe combined organic extract
  6. washwas washed with water, brine
  7. dry with materialdried over magnesium sulphate
  8. customThe solvent was removed
  9. customthe product was purified on a column of silica gel (hexane/EtOAc, 1:1)

Sources & evidence

ORD record
ord-b05c9159c70e49aabdcd77f38c900ca5
Source dataset
uspto-grants-2000_11
Patent number
US06153616

Reaction notes

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