Triphenylphosphine → HCID 68539547, compound

HRID 1992597Notes

Reaction equation

HRID 1992597 reaction equation
[CH3:1][C:2]1[N:7]2N=N[N:10]=[C:6]2[C:5]2[N:11]=[C:12]([CH2:29][CH2:30][CH3:31])[N:13]([CH2:14][CH2:15][CH2:16][O:17][N:18]3C(=O)C4C(=CC=CC=4)C3=O)[C:4]=2[C:3]=1[CH3:32].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClC1C=CC=CC=1Cl>[NH2:18][O:17][CH2:16][CH2:15][CH2:14][N:13]1[C:4]2[C:3]([CH3:32])=[C:2]([CH3:1])[N:7]=[C:6]([NH2:10])[C:5]=2[N:11]=[C:12]1[CH2:29][CH2:30][CH3:31]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 69192599HCID 69192599, compound

Product 1

HCID 68539547HCID 68539547, compoundYield 18.4%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-[3-(5,6-dimethyl-8-propyl-7H-imidazo[4,5-c]tetraazolo[1,5-α]pyridin-7-yl)propoxy]-1H-isoindole-1,3(2H)-dione (8.50 g, 19.6 mmol) and triphenylphosphine (10.3 g, 39.2 mmol) in 1,2-dichlorobenzene (200 mL) was heated at 125° C. for 2 days, then was allowed to stand at room temperature for 3 days. The solvent was removed under reduced pressure. To the resulting residue was added methanol (40 mL) and 1 M HCl (20 mL). The solution was heated at 50° C. for 5 h, then was allowed to cool to room temperature and was concentrated under reduced pressure. Water (20 mL) was added and the mixture was extracted with chloroform (3×10 mL). NaOH (1 M) was added to the aqueous layer to adjust the pH to 11. The aqueous layer was extracted with chloroform (4×30 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with CMA in chloroform) to yield 1.00 g of 1-[3-(aminooxy)propyl]-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-4-amine.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionTo the resulting residue was added methanol (40 mL) and 1 M HCl (20 mL)
  3. temperatureto cool to room temperature
  4. concentrationwas concentrated under reduced pressure
  5. additionWater (20 mL) was added
  6. extractionthe mixture was extracted with chloroform (3×10 mL)
  7. additionNaOH (1 M) was added to the aqueous layer
  8. extractionThe aqueous layer was extracted with chloroform (4×30 mL)
  9. dry with materialThe combined organic layers were dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with CMA in chloroform)

Sources & evidence

ORD record
ord-9ba2e941206c412bb9b00a05f402da79
Source dataset
uspto-grants-2010_01
Patent number
US07648997B2

Reaction notes

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