Triethylamine → HCID 24765745, compound

HRID 1987586Notes

Reaction equation

HRID 1987586 reaction equation
[F:1][C:2]([F:13])([F:12])[CH:3]([C:8]([F:11])([F:10])[F:9])[CH:4]([NH2:7])[CH2:5][OH:6].C(N(CC)CC)C.[F:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>C(Cl)Cl>[F:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:7][CH:4]([CH2:5][OH:6])[CH:3]([C:8]([F:9])([F:10])[F:11])[C:2]([F:12])([F:13])[F:1])(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 451079713,3,3-Trifluoro-2-(trifluoromethyl)-1-(hydroxymethyl)propylamine

Product 1

HCID 24765745HCID 24765745, compoundYield 1.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of 3,3,3-trifluoro-2-(trifluoromethyl)-1-(hydroxymethyl)propyl amine (79 mg, 0.374 mmol) in CH2Cl2 (1 mL) was added triethylamine (0.1 mL, 0.749 mmol) and 4-fluorobenzenesulfonyl chloride (80.5 mg, 0.4 mmol) in CH2Cl2 (1 mL). The solution was stirred for 20 hours at 25° C. and then concentrated. EtOAc (5 mL) was added and the solution was washed with 1M HCl (1 mL), brine (1 mL), dried over Na2SO4 and concentrated. The crude solid was purified by Biotage Flash™ chromatography, eluting with EtOAc/hexanes (1:4), to give 4-fluoro-N-[3,3,3-trifluoro-1-(hydroxymethyl)-2-(trifluoromethyl)propyl]benzene sulfonamide (2.5 mg) as a white solid.

Workup

  1. concentrationconcentrated
  2. additionEtOAc (5 mL) was added
  3. washthe solution was washed with 1M HCl (1 mL), brine (1 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude solid was purified by Biotage Flash™ chromatography
  7. washeluting with EtOAc/hexanes (1:4)

Sources & evidence

ORD record
ord-a4aba6a0035f4a51ab3d1514e3b2a05f
Source dataset
uspto-grants-2009_06
Patent number
US07550629B2

Reaction notes

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