Triethylamine → HCID 86670431, compound

HRID 1972677Notes

Reaction equation

HRID 1972677 reaction equation
Cl.Cl.[F:3][C:4]([F:24])([F:23])[C:5]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[CH:13][CH:12]=1)([OH:10])[C:6]([F:9])([F:8])[F:7].C(N(CC)CC)C.[Cl:32][C:33]1[CH:38]=[CH:37][N:36]=[CH:35][C:34]=1[S:39](Cl)(=[O:41])=[O:40].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:32][C:33]1[CH:38]=[CH:37][N:36]=[CH:35][C:34]=1[S:39]([N:20]1[CH2:21][CH2:22][N:17]([C:14]2[CH:13]=[CH:12][C:11]([C:5]([OH:10])([C:6]([F:9])([F:8])[F:7])[C:4]([F:3])([F:23])[F:24])=[CH:16][CH:15]=2)[CH2:18][CH2:19]1)(=[O:41])=[O:40]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 64222234-Chloropyridine-3-sulfonyl chlorideHCID 866703461,1,1,3,3,3-Hexafluoro-2-(4-(1-piperazinyl)phenyl)-2-propanol dihydrochloride

Product 1

HCID 86670431HCID 86670431, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 20 mL resealable vial was added 1,1,1,3,3,3-hexafluoro-2-(4-(1-piperazinyl)phenyl)-2-propanol dihydrochloride (0.26 g, 0.64 mmol, Example 91, Step 1), DCM (6 mL), triethylamine (0.44 mL, 3.2 mmol) and 4-chloro-3-pyridinesulfonyl chloride (0.16 g, 0.76 mmol). The mixture was stirred at room temperature for 15 min. To the reaction mixture was added saturated aqueous NaHCO3. The mixture was stirred for 5 min and then the solution was transferred onto a phase separation cartridge (Radleys Discovery Technologies) with the organic phase being collected and passed through a plug of Na2SO4. The collected solution was concentrated and purified by silica gel chromatography (0 to 70% EtOAc/hexane) to afford 2-(4-(4-((4-chloro-3-pyridinyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol as a white solid.

Workup

  1. stirringThe mixture was stirred for 5 min
  2. customthe solution was transferred onto a phase separation cartridge (Radleys Discovery Technologies) with the organic phase
  3. custombeing collected
  4. concentrationThe collected solution was concentrated
  5. custompurified by silica gel chromatography (0 to 70% EtOAc/hexane)

Sources & evidence

ORD record
ord-36e69a1846c548eebd255384340424f0
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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