Water → HCID 9843500, compound

HRID 1797189Notes

Reaction equation

HRID 1797189 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:28])([CH3:27])[CH2:19][NH:20][S:21]([CH:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])=[CH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1.C(N(CC)CC)C.O>C1COCC1>[F:28][C:18]([C:15]1[CH:16]=[CH:17][C:12]([C:8]2[CH:7]=[C:6]([NH:5][C:1](=[O:3])[CH3:2])[CH:11]=[CH:10][CH:9]=2)=[CH:13][CH:14]=1)([CH3:27])[CH2:19][NH:20][S:21]([CH:24]([CH3:25])[CH3:26])(=[O:23])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 9863239{2-[4-(3-Aminophenyl)phenyl]-2-fluoropropyl}[(methylethyl)sulfonyl]amine

Product 1

HCID 9843500HCID 9843500, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 100 mL single-neck flask, 49 mg of acetyl chloride was added dropwise to 200 mg of {2-[4-(3-aminophenyl)phenyl]-2-fluoropropyl}[(methylethyl)sulfonyl]amine (prepared in example 5) and 63 mg of triethylamine in THF (25 mL) while stirring under a nitrogen atmosphere at room temperature. The reaction was allowed to stir at this temperature for 2 h. The mixture was then poured into H2O and the desired product was extracted into ethyl acetate. The organic layer was backwashed once with H2O, dried over K2CO3, and concentrated under reduced vacuum to yield 193 mg as a foam. This material was purified via silica gel chromatography employing the Chromatotron, using a 4000 micron rotor and eluting with a solvent of hexane/ethyl acetate 1:1 to yield the title compound (121 mg, 54%) as a white foam. Ion spray M.S. 391.2 (M*−1).

Workup

  1. stirringto stir at this temperature for 2 h
  2. extractionthe desired product was extracted into ethyl acetate
  3. dry with materialdried over K2CO3
  4. concentrationconcentrated under reduced vacuum
  5. customto yield 193 mg as a foam
  6. customThis material was purified via silica gel chromatography
  7. washeluting with a solvent of hexane/ethyl acetate 1:1

Sources & evidence

ORD record
ord-5069f293b73345569b0eb053e3650503
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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