Potassium Carbonate → 2-(4-((2S)-2-((3-ethyl-4-morpholinyl)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol

HRID 1972510Notes

Reaction equation

HRID 1972510 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.[CH2:34]([CH:36]1[CH2:41][O:40][CH2:39][CH2:38][NH:37]1)[CH3:35].C(=O)([O-])[O-].[K+].[K+]>CC#N>[CH2:34]([CH:36]1[CH2:41][O:40][CH2:39][CH2:38][N:37]1[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:14])=[O:15])[CH2:10][CH2:9][N:8]1[C:21]1[CH:22]=[CH:23][C:24]([C:27]([OH:33])([CH3:32])[C:28]([F:31])([F:30])[F:29])=[CH:25][CH:26]=1)[CH3:35]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 142677823-EthylmorpholineHCID 86670301((2R)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl methanesulfonate2×

Product 1

HCID 665823902-(4-((2S)-2-((3-ethyl-4-morpholinyl)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanolYield 31.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

A sealable vial was charged with ((2R)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl methanesulfonate (100 mg, 0.189 mmol, Intermediate B), 3-ethylmorpholine (43.6 mg, 0.378 mmol, ChemBridge Corporation, San Diego, Calif.), potassium carbonate (52.3 mg, 0.378 mmol), and 4 mL of MeCN. The vial was sealed and heated to 150° C. for 90 min. Afterwards, the reaction mixture was filtered and the filtrate was concentrated. The crude material was purified via preparatory TLC using 5% MeOH in CH2Cl2 eluent to yield 2-(4-((2S)-2-((3-ethyl-4-morpholinyl)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol (33 mg) as a mixture of four isomers.

Workup

  1. customThe vial was sealed
  2. filtrationAfterwards, the reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe crude material was purified via preparatory TLC

Sources & evidence

ORD record
ord-8b081dad245f4228aeddf42626ddfede
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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