Triethylamine → HCID 66582305, compound

HRID 1972381Notes

Reaction equation

HRID 1972381 reaction equation
Cl.Cl.[F:3][C:4]([F:22])([F:21])[C:5]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][C@@H:15]2[CH3:20])=[CH:10][CH:9]=1)([OH:7])[CH3:6].C(N(CC)CC)C.[O:30]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31]1>C(Cl)Cl>[F:22][C:4]([F:3])([F:21])[C:5]([C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:19][CH2:18][N:17]([S:35]([C:32]3[CH:33]=[CH:34][O:30][CH:31]=3)(=[O:37])=[O:36])[CH2:16][C@@H:15]2[CH3:20])=[CH:12][CH:13]=1)([OH:7])[CH3:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22179302Furan-3-sulfonyl chlorideHCID 66582500HCID 66582500, compound

Product 1

HCID 66582305HCID 66582305, compoundYield 21.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1,1-trifluoro-2-(4-((2S)-2-methyl-1-piperazinyl)phenyl)-2-propanol dihydrochloride (100 mg, 0.277 mmol) and triethylamine (0.115 mL, 0.830 mmol) in CH2Cl2 (4.0 mL) was added 3-furansulfonyl chloride (55.3 mg, 0.332 mmol, Ryan Scientific, Inc., Mt. Pleasant, S.C.). After 30 min at room temperature, the reaction was concentrated and purified via column chromatography (12 g of silica, 0 to 70% EtOAc in hexanes) to yield 1,1,1-trifluoro-2-(4-((2S)-4-(3-furanylsulfonyl)-2-methyl-1-piperazinyl)phenyl)-2-propanol (25 mg) as a mixture of two isomers.

Workup

  1. concentrationthe reaction was concentrated
  2. custompurified via column chromatography (12 g of silica, 0 to 70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1cad1506738f4f6bb0a471167b9784f9
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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