Hydrochloric Acid → HCID 68912078, compound

HRID 729513Notes

Reaction equation

HRID 729513 reaction equation
C(OC([N:8]1[CH2:13][CH:12]2[CH2:14][C:9]1=[CH:10][N:11]2[C:15]1[N:20]2[CH:21]=[N:22][N:23]=[C:19]2[CH:18]=[C:17]([C:24]2[CH:29]=[CH:28][N:27]=[C:26]([NH:30][CH:31]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH3:32])[CH:25]=2)[N:16]=1)=O)(C)(C)C.Cl>O1CCOCC1.CO>[C@H:12]12[CH2:14][C@H:9]([NH:8][CH2:13]1)[CH2:10][N:11]2[C:15]1[N:23]2[N:22]=[CH:21][N:20]=[C:19]2[CH:18]=[C:17]([C:24]2[CH:29]=[CH:28][N:27]=[C:26]([NH:30][C@H:31]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH3:32])[CH:25]=2)[N:16]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68911548HCID 68911548, compound

Product 1

HCID 68912078HCID 68912078, compound

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 312751,4-DioxaneSolvent

Procedure

To 5-{7-[2-(1-phenyl-ethylamino)-pyridin-4-yl]-[1,2,4]triazolo[4,3-c)pyrimidin-5-yl}-2,5-diaza-bicyclo[2.2.1]heptene-2-carboxylic acid tert-butyl ester (0.022 g, 0.043 mmol) were added 4N HCl (1 mL) in dioxane and a few drops of methanol. After 1 h, the reaction was concentrated in vacuo and the residue was taken up in water and extracted with ethyl acetate. The aqueous layer was neutralized with saturated sodium bicarbonate and extracted with chloroform (3×). The combined organic extract was dried (K2CO3), filtered, and concentrated in vacuo to give the title compound as a golden yellow solid. MS (ES+): 413.1 [M+H]+, 411.2 [M−H]−.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. extractionextracted with ethyl acetate
  3. extractionextracted with chloroform (3×)
  4. extractionThe combined organic extract
  5. dry with materialwas dried (K2CO3)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-059d8d4a54214e408698523936d3cd05
Source dataset
uspto-grants-2009_09
Patent number
US07582631B2

Reaction notes

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