Methanesulfonyl chloride → HCID 56932775, compound

HRID 1972581Notes

Reaction equation

HRID 1972581 reaction equation
[F:1][C:2]([F:35])([F:34])[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][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:8][CH:7]=1)([OH:5])[CH3:4].[CH3:36][S:37](Cl)(=[O:39])=[O:38].CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:28]1([N:27]([CH2:26][C@H:13]2[CH2:14][N:15]([S:18]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)(=[O:20])=[O:19])[CH2:16][CH2:17][N:12]2[C:9]2[CH:8]=[CH:7][C:6]([C:3]([OH:5])([CH3:4])[C:2]([F:1])([F:34])[F:35])=[CH:11][CH:10]=2)[S:37]([CH3:36])(=[O:39])=[O:38])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 665825861,1,1-trifluoro-2-(4-((2S)-2-((phenylamino)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol

Product 1

HCID 56932775HCID 56932775, compoundYield 29.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1,1-trifluoro-2-(4-((2S)-2-((phenylamino)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol (0.100 g, 0.190 mmol, Example 203) in CH2Cl2 (3.0 mL) was added 4-dimethylaminopyridine (0.0046 g, 0.038 mmol), methanesulfonyl chloride (0.044 g, 0.381 mmol) and Hünig's base (0.135 mL, 0.774 mmol). After 15 h at room temperature, the solvent was removed and the crude product was purified by column chromatography (24 g of silica gel, 10 to 40% acetone in hexanes) to give N-phenyl-N-(((2R)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)methanesulfonamide (0.034 g) as a mixture of two isomers.

Workup

  1. customthe solvent was removed
  2. customthe crude product was purified by column chromatography (24 g of silica gel, 10 to 40% acetone in hexanes)

Sources & evidence

ORD record
ord-42a3073fd04e4c8495279d53b4c01204
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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