Hydrochloric Acid → HCID 131735176, compound

HRID 623303Notes

Reaction equation

HRID 623303 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]2=[N:15][C:16](=S)[C:17]([F:20])([F:19])[F:18])=[CH:4][CH:3]=1.Cl.[NH2:23][OH:24].C(N(CC)CC)C.Cl>C(OCC)(=O)C.C(O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]2=[N:15][C:16](=[N:23][OH:24])[C:17]([F:20])([F:19])[F:18])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 71698838HCID 71698838, compound

Product 1

HCID 131735176HCID 131735176, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

25 ml of ethanol was added to 1.00 g (3.00 mmol) of the N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide (1-20) 1 synthesized by the method in Synthetic Example 4, 1.04 g (15.0 mmol) of hydroxylamine hydrochloride and 2.00 ml (1.50 g, 15.0 mmol) of triethylamine were added thereto in sequence, and the resulting mixture was stirred at 50° C. for 21.5 hours. After the reaction was completed, ethyl acetate and 1% hydrochloric acid were added to the reaction solution to perform liquid separation, and the organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The organic layer was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain the subject material. Amount obtained 625 mg (yield 63%).

Workup

  1. additionwere added
  2. customliquid separation
  3. washthe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe organic layer was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)
  7. customto obtain the subject material
  8. customAmount obtained 625 mg (yield 63%)

Sources & evidence

ORD record
ord-a07648af8e82443ea22abc7cb4dc32ab
Source dataset
uspto-grants-2016_04
Patent number
US09301525B2

Reaction notes

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