Triethylamine → (4-(2-Thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl methanesulfonate

HRID 1972406Notes

Reaction equation

C([O:8][CH2:9][CH:10]1[CH2:15][N:14]([S:16]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)(=[O:18])=[O:17])[CH2:13][CH2:12][N:11]1[C:24]1[CH:29]=[CH:28][C:27]([C:30]([OH:36])([CH3:35])[C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=1)C1C=CC=CC=1.C(N(CC)CC)C.[CH3:44][S:45](Cl)(=[O:47])=[O:46]>C(Cl)Cl>[CH3:44][S:45]([O:8][CH2:9][CH:10]1[CH2:15][N:14]([S:16]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:18])[CH2:13][CH2:12][N:11]1[C:24]1[CH:25]=[CH:26][C:27]([C:30]([OH:36])([CH3:35])[C:31]([F:34])([F:32])[F:33])=[CH:28][CH:29]=1)(=[O:47])=[O:46]

Participants

Conditions

Temperature: 0 °C

Procedure

A 25-mL round bottomed flask was charged with 1,1,1-trifluoro-2-(4-(2-(hydroxymethyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol (400 mg, 0.888 mmol, Example 44), triethylamine (136 μL, 0.977 mmol) and CH2Cl2 (5 mL). After cooling to 0° C., methanesulfonyl chloride (69.2 μL, 0.888 mmol) was slowly added via syringe. The reaction was then warmed to room temperature and stirred for 3 h. After this time, the mixture was concentrated and the crude material was purified by column chromatography (12 g silica gel, 5%-80% (10% MeOH—CH2Cl2) in CH2Cl2) to give (4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl methanesulfonate (403 mg) as a colorless foam.

Workup

temperatureThe reaction was then warmed to room temperature
concentrationAfter this time, the mixture was concentrated
customthe crude material was purified by column chromatography (12 g silica gel, 5%-80% (10% MeOH—CH2Cl2) in CH2Cl2)

Sources & evidence

ORD record: ord-242d2d1198864204a6acd62737d1f5d4
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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