Trifluoroacetic acid → HCID 21913227, compound

HRID 1245980Notes

Reaction equation

HRID 1245980 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([C:10]1[N:11]([CH2:24][CH2:25][O:26][CH2:27][CH2:28][NH:29]C(=O)OC(C)(C)C)[C:12]2[C:17]([CH3:18])=[C:16]([CH3:19])[N:15]3[N:20]=[N:21][N:22]=[C:14]3[C:13]=2[N:23]=1)[CH3:9]>ClCCl>[CH2:8]([C:10]1[N:11]([CH2:24][CH2:25][O:26][CH2:27][CH2:28][NH2:29])[C:12]2[C:17]([CH3:18])=[C:16]([CH3:19])[N:15]3[N:20]=[N:21][N:22]=[C:14]3[C:13]=2[N:23]=1)[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21913379HCID 21913379, compound

Product 1

HCID 21913227HCID 21913227, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of trifluoroacetic acid (188 mL, 2.44 mol) in dichloromethane (300 mL) was cooled to 0° C. A solution of tert-butyl 2-{2-[(8-ethyl-5,6-dimethyl-7H-imidazo[4,5-c]tetrazolo[1,5-a]pyridin-7-yl)]ethoxy}ethylcarbamate (19.7 g, 48.8 mmol) in dichloromethane (300 mL) was then slowly added over a period of 30 minutes, and the reaction was stirred overnight. The volatiles were removed under reduced pressure, and the residual brown oil was stirred with 2-propanol (300 mL) to form a white salt, which was isolated by filtration and dried in a vacuum at 80° C. The salt was dissolved in water (200 mL), and solid sodium carbonate was added to adjust to pH 12. The solution was extracted with chloroform overnight with a continuous extractor. The extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 11.5 g of 2-[2-(8-ethyl-5,6-dimethyl-7H-imidazo[4,5-c]tetrazolo[1,5-a]pyridin-7-yl)ethoxy]ethylamine as a white solid, m. p. 181–183° C.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. stirringthe residual brown oil was stirred with 2-propanol (300 mL)
  3. customto form a white salt
  4. customwhich was isolated by filtration
  5. customdried in a vacuum at 80° C
  6. dissolutionThe salt was dissolved in water (200 mL)
  7. additionsolid sodium carbonate was added
  8. extractionThe solution was extracted with chloroform overnight with a continuous extractor
  9. dry with materialThe extracts were dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-002cc06a8d4b4ac3aa6bdc7beae3908d
Source dataset
uspto-grants-2006_10
Patent number
US07125890B2

Reaction notes

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