Trifluoroacetic acid → HCID 21913469, compound

HRID 1008080Notes

Reaction equation

HRID 1008080 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]2[C:24]3[C:23]([CH3:25])=[C:22]([CH3:26])[N:21]4N=N[N:29]=[C:20]4[C:19]=3[N:18]=[C:17]2[CH2:30][CH2:31][CH3:32])(=[O:10])=[O:9])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>[Pt](=O)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]2[C:24]3[C:23]([CH3:25])=[C:22]([CH3:26])[N:21]=[C:20]([NH2:29])[C:19]=3[N:18]=[C:17]2[CH2:30][CH2:31][CH3:32])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21913847HCID 21913847, compound

Product 1

HCID 21913469HCID 21913469, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

A mixture of 7-[5-(4-fluorobenzenesulfonyl)pentyl]-5,6-dimethyl-8-propyl-7H-imidazo[4,5-c]tetrazolo[1,5-a]pyridine (1.61 g, 3.51 mmol), trifluoroacetic acid (15 mL) and platinum (IV) oxide were added to a Parr vessel and agitated under hydrogen pressure (50 psi, 3.4×105 Pa) for two days. The reaction mixture was filtered through a layer of CELITE filter aid, and the filter cake was washed with methanol. The filtrate was concentrated under reduced pressure, and the black residue was stirred in concentrated hydrochloric acid (10 mL) for 1.5 hours. The solution was treated with 1 N aqueous sodium hydroxide (100 mL) and solid sodium hydroxide until the solution exhibited a pH of 14. The solution was extracted with chloroform (3×80 mL), and the combined extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide 1.8 g of the crude product as a white foam. The crude product was purified by column chromatography on silica gel (eluting with 98:2 chloroform:methanol) and recrystallized from ethyl acetate:hexane. The solid was triturated with ethyl acetate and dried at 70° C. in a vacuum oven overnight to provide 0.57 g of 1-[5-(4-fluorobenzenesulfonyl)pentyl]-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-4-amine as a white powder, mp 130.0-132.0° C.

Workup

  1. additionwere added to a Parr vessel
  2. filtrationThe reaction mixture was filtered through a layer of CELITE
  3. filtrationfilter aid
  4. washthe filter cake was washed with methanol
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. stirringthe black residue was stirred in concentrated hydrochloric acid (10 mL) for 1.5 hours
  7. additionThe solution was treated with 1 N aqueous sodium hydroxide (100 mL) and solid sodium hydroxide until the solution
  8. extractionThe solution was extracted with chloroform (3×80 mL)
  9. dry with materialthe combined extracts were dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customto provide 1.8 g of the crude product as a white foam
  13. customThe crude product was purified by column chromatography on silica gel (eluting with 98:2 chloroform:methanol)
  14. customrecrystallized from ethyl acetate
  15. customThe solid was triturated with ethyl acetate
  16. customdried at 70° C. in a vacuum oven overnight

Sources & evidence

ORD record
ord-9de603d43edd423ab784473653d55e37
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

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