Triethylamine → HCID 10204509, compound

HRID 1072675Notes

Reaction equation

HRID 1072675 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:24]=[CH:23][C:11]([O:12][CH:13]([CH3:22])[CH2:14][NH:15][S:16]([CH:19]([CH3:21])[CH3:20])(=[O:18])=[O:17])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:32][CH:33]([S:35](Cl)(=[O:37])=[O:36])[CH3:34]>C(Cl)Cl>[CH3:20][CH:19]([S:16]([NH:15][CH2:14][CH:13]([O:12][C:11]1[CH:10]=[CH:9][C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][S:35]([CH:33]([CH3:34])[CH3:32])(=[O:37])=[O:36])[CH:3]=2)=[CH:24][CH:23]=1)[CH3:22])(=[O:18])=[O:17])[CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 824082-Propanesulfonyl chlorideHCID 10132502HCID 10132502, compound

Product 1

HCID 10204509HCID 10204509, compoundYield 264.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of {2-[4-(3-aminophenyl)phenoxy]propyl}[(methylethyl)sulfonyl]amine (125 mg, 0.3587 mmol, prepared in example 3) dissolved in methylene chloride (2.5 mL, anhydrous) was added triethylamine (0.125 mL, 0.8968 mmol) under a nitrogen system. The mixture was cooled to 0° C. and 2-propanesulfonyl chloride (0.06 mL, 0.5381 mmol) was added by syringe. The mixture was allowed to warm to room temperature, and stirred overnight, under a nitrogen system. The reaction was quenched with excess water, and the organic layer was dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure, yielding 431 mg viscous oil. Purification was conducted using a Chromatotron®, on a 4000 μm rotor and eluting with a 1:1 hexane:ethyl acetate solvent system, yielding 400 mg of two inseparable coeluting spots. This mixture was purified by reverse phase chromatography on a Vydac C-18 column on a gradient of 5 to 70% of 0.1% trifluoroacetic acid/acetonitrile in water over 45 minutes at 200 mL/min elution rate, yielding the title compound (16.7 mg, 1%) as a slow crystallizing foam.

Workup

  1. temperatureto warm to room temperature
  2. customThe reaction was quenched with excess water
  3. dry with materialthe organic layer was dried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-78bdd476fa934914a33f783df4075c4c
Source dataset
uspto-grants-2005_06
Patent number
US06911476B2

Reaction notes

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