Methanesulfonyl chloride → HCID 56932774, compound

HRID 1972577Notes

Reaction equation

HRID 1972577 reaction equation
[CH:1]1([NH:4][CH2:5][C@H:6]2[CH2:11][N:10]([S:12]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)(=[O:14])=[O:13])[CH2:9][CH2:8][N:7]2[C:20]2[CH:25]=[CH:24][C:23]([C:26]([OH:32])([CH3:31])[C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=2)[CH2:3][CH2:2]1.[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>[CH:1]1([N:4]([CH2:5][C@H:6]2[CH2:11][N:10]([S:12]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)(=[O:14])=[O:13])[CH2:9][CH2:8][N:7]2[C:20]2[CH:25]=[CH:24][C:23]([C:26]([OH:32])([CH3:31])[C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=2)[S:34]([CH3:33])(=[O:36])=[O:35])[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 66582354HCID 66582354, compound

Product 1

HCID 56932774HCID 56932774, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-((2S)-2-((cyclopropylamino)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol (0.130 g, 0.258 mmol, Example 199) in CH2Cl2 (5.0 mL) was added 4-dimethylaminopyridine (0.006 g, 0.052 mmol), methanesulfonyl chloride (0.059 g, 0.516 mmol) and Hünig's base (0.135 mL, 0.774 mmol). After 20 min at room temperature, the solvent was concentrated and the crude product was purified by column chromatography (40 g of silica gel, 10 to 30% acetone in hexanes) to give N-cyclopropyl-N-(((2R)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)methanesulfonamide (0.100 g) as a mixture of two isomers.

Workup

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

Sources & evidence

ORD record
ord-eac49752e40047a19356a505069bf712
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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