Methanesulfonyl chloride → HCID 66582687, compound

HRID 1972572Notes

Reaction equation

HRID 1972572 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([S:18]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)(=[O:20])=[O:19])[CH2:14][C@@H:13]2[CH2:26][NH:27][CH:28]([CH3:30])[CH3:29])=[CH:8][CH:7]=1)([OH:5])[CH3:4].[CH3:33][S:34](Cl)(=[O:36])=[O:35].CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:30][CH:28]([N:27]([CH2:26][C@H:13]1[CH2:14][N:15]([S:18]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)(=[O:20])=[O:19])[CH2:16][CH2:17][N:12]1[C:9]1[CH:8]=[CH:7][C:6]([C:3]([OH:5])([CH3:4])[C:2]([F:1])([F:31])[F:32])=[CH:11][CH:10]=1)[S:34]([CH3:33])(=[O:36])=[O:35])[CH3:29]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 66582708HCID 66582708, compound

Product 1

HCID 66582687HCID 66582687, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1,1-trifluoro-2-(4-((2S)-2-(((1-methylethyl)amino)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol (0.150 g, 0.305 mmol) in CH2Cl2 (5.0 mL) was added 4-dimethylaminopyridine (7.5 mg, 0.062 mmol), methanesulfonyl chloride (0.05 mL, 0.61 mmol, Aldrich, St. Louis, Mo.), and Hünig's base (0.2 mL, 0.9 mmol). The reaction mixture was stirred at room 20 min and then the solvent was removed in vacuo. The crude product was purified by column chromatography (40 g of silica, 10% to 30% acetone in hexanes) to afford N-(1-methylethyl)-N-(((2R)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)methanesulfonamide (0.110 g) as a mixture of two isomers:

Workup

  1. customthe solvent was removed in vacuo
  2. customThe crude product was purified by column chromatography (40 g of silica, 10% to 30% acetone in hexanes)

Sources & evidence

ORD record
ord-9ec88f9b30344c2b97b3a7e8865881a5
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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