Potassium Carbonate → HCID 56933046, compound

HRID 1972407Notes

Reaction equation

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

Participants

Conditions

Temperature: 150 °C

Procedure

A 20 mL vial was charged with (4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl methanesulfonate (75 mg, 0.142 mmol), (S)-3-methylmorpholine (28.7 mg, 0.284 mmol Sigma-Aldrich, St. Louis, Mo.), potassium carbonate (39.2 mg, 0.284 mmol), and acetonitrile (4 mL). The vial was sealed and heated at 150° C. for 90 min in a microwave reactor (Emrys Optimizer Automated Microwave Synthesizer, Uppsala, Sweden). After this time, the mixture was filtered and the filtrate was concentrated. The crude material was purified via preparatory silica gel TLC (5% MeOH in CH2Cl2) to give 1,1,1-trifluoro-2-(4-(2-(((3S)-3-methyl-4-morpholinyl)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol as a mixture of four isomers.

Workup

customThe vial was sealed
filtrationAfter this time, the mixture was filtered
concentrationthe filtrate was concentrated
customThe crude material was purified via preparatory silica gel TLC (5% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-e4b8eae2b8e947a185b8c389e436d414
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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