Potassium Carbonate → HCID 66583414, compound

HRID 1972555Notes

Reaction equation

HRID 1972555 reaction equation
CS(O[CH2:6][C@H:7]1[CH2:12][N:11]([S:13]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)(=[O:15])=[O:14])[CH2:10][CH2:9][N:8]1[C:21]1[CH:26]=[CH:25][C:24]([C:27]([OH:33])([CH3:32])[C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=1)(=O)=O.[CH3:34][C:35]1([CH3:42])[NH:40][CH2:39][CH2:38][NH:37][C:36]1=[O:41].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:34][C:35]1([CH3:42])[N:40]([CH2:6][C@H:7]2[CH2:12][N:11]([S:13]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)(=[O:14])=[O:15])[CH2:10][CH2:9][N:8]2[C:21]2[CH:22]=[CH:23][C:24]([C:27]([OH:33])([CH3:32])[C:28]([F:31])([F:30])[F:29])=[CH:25][CH:26]=2)[CH2:39][CH2:38][NH:37][C:36]1=[O:41]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2111572-Piperazinone, 3,3-dimethyl-HCID 86670301((2R)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl methanesulfonate2×

Product 1

HCID 66583414HCID 66583414, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following the procedure reported for Example 179, the reaction of ((2R)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl methanesulfonate (102 mg, 0.193 mmol, Intermediate B), 3,3-dimethylpiperazin-2-one (26.0 mg, 0.203 mmol, ChemBridge, San Diego, Calif.), and potassium carbonate (80 mg, 0.579 mmol, Sigma-Aldrich, St. Louis, Mo.) in acetonitrile (1.286 mL). Purification by silica gel chromatography (1.5 to 7% MeOH in CH2Cl2 gradient) delivered the title compound as a mixture of two isomers.

Workup

  1. customPurification by silica gel chromatography (1.5 to 7% MeOH in CH2Cl2 gradient)
  2. additionas a mixture of two isomers

Sources & evidence

ORD record
ord-7e02ed59b8eb42788e1cbf42de4af0e1
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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