Propargylamine → HCID 17961246, compound

HRID 901823Notes

Reaction equation

HRID 901823 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[S:9](Cl)(=[O:11])=[O:10].[CH2:15]([NH2:18])[C:16]#[CH:17]>O1CCOCC1.Cl>[CH2:15]([NH:18][S:9]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:3]=1[C:2]([F:14])([F:13])[F:1])(=[O:11])=[O:10])[C:16]#[CH:17]

Participants

5

Reactant 2

HCID 239041PropargylamineHCID 179612474-(trifluoroMethyl)pyridine-3-sulfonyl chloride

Product 1

HCID 17961246HCID 17961246, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

4-Trifluoromethyl-pyridine-3-sulfonyl chloride (0.45 g) was dissolved in dioxane (3 ml), and pro-pargylamine (0.63 ml) was added to the mixture and allowed to stand at ambient temperature overnight. The reaction was diluted with 0.5% HCl and 37% HCl was added drop-wise until the mixture became acidic. This was extracted three times with-ethyl acetate. The ethyl acetate portions were combined, washed with saturated sodium bicarbonate and dried with magnesium sulfate. The drying agent was filtered away and the solvent evaporated to give 0.13 g of crude 4-tri-fluoromethyl-pyridine-3-sulfonic acid prop-2-ynylamide, which was chromatographed an silica gel using ethyl acetate and methylene chloride to yield 0.08 g of purified 4-Trifluoromethyl-pyridine-3-sulfonic acid prop-2-ynylamide. LC/ms analysis with RT=1.36 min yielded a purity of 98% m+/m− of 264.8/262.9. Melting-point of the purified compound tested as 97-98° C.

Workup

  1. additionwas added drop-wise until the mixture
  2. extractionThis was extracted three times with-ethyl acetate
  3. washwashed with saturated sodium bicarbonate
  4. dry with materialdried with magnesium sulfate
  5. filtrationThe drying agent was filtered away
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-07f8a55f9fad4de389e0b50ea202376f
Source dataset
uspto-grants-2008_04
Patent number
US07365042B2

Reaction notes

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