Triethylamine → HCID 22388583, compound
Reaction equation
N[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:27](CC)CC)C.[C:32](Cl)(=[O:36])[CH:33]([CH3:35])[CH3:34]>C(Cl)Cl>[CH3:34][CH:33]([CH3:35])[C:32]([NH:27][C:7]1[CH:6]=[CH:5][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:3][CH:2]=1)=[O:36]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of {2-[4-(3-aminophenyl)phenoxy]propyl}[(methylethyl)sulfonyl]amine (145 mg, 0.416 mmol, prepared in example 3) dissolved in methylene chloride (2.8 mL, anhydrous), was added triethylamine (0.15 mL, 1.04 mmol) under a nitrogen system. The mixture was cooled to 0° C. and isobutyryl chloride (0.13 mL, 1.25 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 vacuum, yielding 280 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 (136 mg, 78%) as a slow crystallizing foam.
Workup
- temperatureto warm to room temperature
- customThe reaction was quenched with excess water
- dry with materialthe organic layer was dried with anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced vacuum
Sources & evidence
- ORD record
- ord-be1ccf8ae0e4424a9718b8627447858e
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06911476B2
Reaction notes
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