Ethylamine → HCID 9866055, compound

HRID 1797188Notes

Reaction equation

HRID 1797188 reaction equation
C(Cl)(=O)C(Cl)=O.[F:7][C:8]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:32]=[CH:31][C:27]([C:28]([OH:30])=O)=[CH:26][CH:25]=2)=[CH:20][CH:19]=1)([CH3:17])[CH2:9][NH:10][S:11]([CH:14]([CH3:16])[CH3:15])(=[O:13])=[O:12].[CH2:33]([NH2:35])[CH3:34]>C(Cl)Cl.CN(C=O)C.C1COCC1>[CH2:33]([NH:35][C:28]([C:27]1[CH:26]=[CH:25][C:24]([C:21]2[CH:20]=[CH:19][C:18]([C:8]([F:7])([CH3:17])[CH2:9][NH:10][S:11]([CH:14]([CH3:15])[CH3:16])(=[O:13])=[O:12])=[CH:23][CH:22]=2)=[CH:32][CH:31]=1)=[O:30])[CH3:34]

Participants

7

Reactant 3

HCID 6341EthylamineHCID 65578Oxalyl chlorideHCID 221765834-[4-(1-fluoro-1-methyl-2-{[(methylethyl)sulfonyl]amino}ethyl)phenyl]benzoic Acid

Product 1

HCID 9866055HCID 9866055, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Into a 50 mL single neck flask, 1 mL oxalyl chloride was added syringe wise to 4-[4-(1-fluoro-1-methyl-2-{[(methylethyl)sulfonyl]amino}ethyl)phenyl]benzoic acid (140 mg, 0.37 mmol, prepared in example 4) in CH2Cl2 (10 mL) while stirring under nitrogen at room temperature. Immediately, 1 drop of DMF was added by pipette initiating a foaming of the mixture. The reaction was stirred one hour at this temperature and then concentrated under reduced vacuum to yield a white semi-solid. This material was placed into THF (10 mL) and added dropwise to a stirring solution of 2.0 M ethylamine in THF (0.5 mL) at room temperature and the mixture was stirred overnight. In the morning, the solution was concentrated under reduced vacuum and the resulting oil was taken into CH2Cl2 and the organic layer was washed once with H2O, dried over K2CO3, and concentrated under reduced vacuum to yield 151 mg as an oil. This material was purified via silica gel chromatography employing the Chromatotron and using a 2000 micron rotor while eluting with a solvent of methylene chloride/ethyl acetate 1:1 to yield the title compound (127 mg, 85%) as a viscous oil. Ion spray M.S. 407.4 (M*+1).

Workup

  1. stirringThe reaction was stirred one hour at this temperature
  2. concentrationconcentrated under reduced vacuum
  3. customto yield a white semi-solid
  4. stirringthe mixture was stirred overnight
  5. concentrationIn the morning, the solution was concentrated under reduced vacuum
  6. washthe organic layer was washed once with H2O
  7. dry with materialdried over K2CO3
  8. concentrationconcentrated under reduced vacuum
  9. customto yield 151 mg as an oil
  10. customThis material was purified via silica gel chromatography
  11. washwhile eluting with a solvent of methylene chloride/ethyl acetate 1:1

Sources & evidence

ORD record
ord-42aa19350bf34bdf864e62acbd448928
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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