Triethylamine → HCID 10140787, compound

HRID 1072680Notes

Reaction equation

HRID 1072680 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:27]=[CH:26][C:14]([O:15][CH:16]([CH3:25])[CH2:17][NH:18][S:19]([CH:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.C(N(CC)CC)C.[CH3:35][CH:36]([S:38](Cl)(=[O:40])=[O:39])[CH3:37]>C(Cl)Cl>[CH3:24][CH:22]([S:19]([NH:18][CH2:17][CH:16]([O:15][C:14]1[CH:26]=[CH:27][C:11]([C:8]2[CH:7]=[CH:6][C:5]([CH2:4][CH2:3][NH:2][S:38]([CH:36]([CH3:37])[CH3:35])(=[O:40])=[O:39])=[CH:10][CH:9]=2)=[CH:12][CH:13]=1)[CH3:25])(=[O:21])=[O:20])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 824082-Propanesulfonyl chlorideHCID 22388593HCID 22388593, compound

Product 1

HCID 10140787HCID 10140787, compoundYield 137.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 10 mL round-bottomed flask, in an ice bath, fitted with a thermometer, and under a nitrogen atmosphere, of (2-{4-[4-(2-aminoethyl)phenyl]phenoxy}propyl)[(methylethyl)sulfonyl]amine hydrochloride (150 mg, 0.3984 mmol, prepared in example 39) dissolved in methylene chloride (2.7 mL) was added triethylamine (0.07 mL, 0.478 mmol). Once the mixture was cooled to 0° C., 2-propanesulfonyl chloride (0.05 mL, 0.4382 mmol) was added by syringe, and the mixture was gradually warmed to room temperature, with stirring overnight. The reaction was quenched with excess water, and the organic layer was dried with anhydrous sodium sulfate, filtered, and concentrated under vacuum, yielding 265 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 the title compound (200 mg, 100%) as a slow crystallizing foam.

Workup

  1. customTo a 10 mL round-bottomed flask, in an ice bath, fitted with a thermometer
  2. temperaturethe mixture was gradually warmed to room temperature
  3. customThe reaction was quenched with excess water
  4. dry with materialthe organic layer was dried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-fa577cee24de45f5b4a6bb0d89f4e9ca
Source dataset
uspto-grants-2005_06
Patent number
US06911476B2

Reaction notes

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