Methylamine → HCID 9930416, compound

HRID 1797186Notes

Reaction equation

HRID 1797186 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](O)=[O:29])=[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].O1CCOCC1.[CH3:39][NH2:40]>C(Cl)Cl.CN(C=O)C>[F:7][C:8]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:32]=[CH:31][C:27]([C:28]([NH:40][CH3:39])=[O:29])=[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]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 312751,4-DioxaneHCID 65578Oxalyl chlorideHCID 221765834-[4-(1-fluoro-1-methyl-2-{[(methylethyl)sulfonyl]amino}ethyl)phenyl]benzoic Acid

Product 1

HCID 9930416HCID 9930416, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

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 (300 mg, 0.79 mmol, prepared in example 1a) in methylene chloride (15 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 dioxane (20 mL) and added dropwise to a stirring solution of 40% methylamine (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 methylene chloride and the organic layer was washed once with H2O, dried over K2CO3, filtered, and concentrated under reduced vacuum to yield 391 mg as a solid. This material was purified via recrystallization from hexane/ethyl acetate 1:1 to yield the title compound (231 mg, 49%) as a white solid. Ion spray M.S. 391.4 (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. filtrationfiltered
  9. concentrationconcentrated under reduced vacuum
  10. customto yield 391 mg as a solid
  11. customThis material was purified via recrystallization from hexane/ethyl acetate 1:1

Sources & evidence

ORD record
ord-7ac3b3a19dc749bbbbc6211b17ce5339
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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