Propyl isocyanate → HCID 123792055, compound

HRID 623304Notes

Reaction equation

HRID 623304 reaction equation
[CH2:1]([N:4]=[C:5]=[O:6])[CH2:2][CH3:3].[Cl:7][C:8]1[N:13]=[CH:12][C:11]([CH2:14][N:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]2=[N:21][C:22](=[N:27][OH:28])[C:23]([F:26])([F:25])[F:24])=[CH:10][CH:9]=1.CC(C)([O-])C.[K+]>C(#N)C>[Cl:7][C:8]1[N:13]=[CH:12][C:11]([CH2:14][N:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]2=[N:21][C:22](=[N:27][O:28][C:5](=[O:6])[NH:4][CH2:1][CH2:2][CH3:3])[C:23]([F:24])([F:25])[F:26])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 61033Propyl isocyanateHCID 23665647Potassium tert-butoxideHCID 131735176HCID 131735176, compound

Product 1

HCID 123792055HCID 123792055, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5 ml of anhydrous acetonitrile was added to 11 mg (0.13 mmol) of normal propyl isocyanate, 40 mg (0.12 mmol) of the N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-hydroxyacetimidamide (1-499) synthesized by the method in Synthetic Example 7 and 4 mg (0.04 mmol) of potassium-t-butoxide were added thereto, and the resulting mixture was stirred at room temperature for 1 hour. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and ethyl acetate and a saturated saline solution were added thereto to perform liquid separation. The ethyl acetate layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure and purified by a TLC plate (one sheet of 0.5 mm plate, evolved with hexane:ethyl acetate=1:3) to obtain the subject material. Amount obtained 16 mg (yield 32%).

Workup

  1. additionwere added
  2. concentrationthe reaction solution was concentrated under reduced pressure, and ethyl acetate
  3. additiona saturated saline solution were added
  4. customliquid separation
  5. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. custompurified by a TLC plate (one sheet of 0.5 mm plate, evolved with hexane:ethyl acetate=1:3)
  8. customto obtain the subject material
  9. customAmount obtained 16 mg (yield 32%)

Sources & evidence

ORD record
ord-684e078cbfe846fa8b55566072898f00
Source dataset
uspto-grants-2016_04
Patent number
US09301525B2

Reaction notes

Loading…