Water → HCID 86601755, compound

HRID 1593375Notes

Reaction equation

HRID 1593375 reaction equation
[CH3:1][C@@H:2]1[CH2:7][NH:6][C@@H:5]([CH3:8])[CH2:4][N:3]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[F:16][C:17]1[CH:24]=[C:23](F)[CH:22]=[CH:21][C:18]=1[C:19]#[N:20].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN1C(=O)N(C)CC1.C(#N)C>[C:19]([C:18]1[CH:21]=[CH:22][C:23]([N:6]2[C@@H:5]([CH3:8])[CH2:4][N:3]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[C@H:2]([CH3:1])[CH2:7]2)=[CH:24][C:17]=1[F:16])#[N:20]

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 775452,4-DifluorobenzonitrileHCID 24903576tert-butyl (2R,5S)-2,5-dimethylpiperazine-1-carboxylate

Product 1

HCID 86601755HCID 86601755, compoundYield 38.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Conditions

Temperature
120 °C

Procedure

Into a solution of 9.74 g of tert-butyl (2R,5S)-2,5-dimethylpiperazine-1-carboxylate in 25 ml of DMI and 25 ml of acetonitrile were added 5 g of 2,4-difluorobenzonitrile and 11.4 g of cesium carbonate, followed by 2 days of stirring at 120° C. The reaction solution was poured into water, followed by extraction with ethyl acetate. After the organic layer was washed with saturated saline, it was dried over anhydrous sodium sulfate. The solvent was removed by evaporation and the resulting residue was purified by silica gel column chromatography to obtain 4.66 g of the title compound from an eluate eluted with hexane-ethyl acetate (80:20, v/v).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washAfter the organic layer was washed with saturated saline, it
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. customThe solvent was removed by evaporation
  5. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-91cba06c6a8e4baa97ec10fcd299d49a
Source dataset
uspto-grants-2007_11
Patent number
US07297698B2

Reaction notes

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