Hydrochloric Acid → HCID 68912633, compound

HRID 729515Notes

Reaction equation

HRID 729515 reaction equation
C(OC([N:8]1[CH2:13][CH:12]2[CH2:14][CH:9]1[CH2:10][N:11]2[C:15]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([NH:27][CH:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH3:29])[CH:22]=2)[CH:18]=[CH:17][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[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C@H:28]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH3:29])[CH:22]=2)[CH:18]=[CH:17][N:16]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68908063HCID 68908063, compound

Product 1

HCID 68912633HCID 68912633, compound

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 312751,4-DioxaneSolvent

Procedure

To 5-[2′-(1-phenyl-ethylamino)-[4,4′]bipyridinyl-2-yl]-2,5-diazabicyclo[2.2.1]-heptane-2-carboxylic acid tert-butyl ester (0.027 g, 0.058 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+): 372.4 [M+H]+, 370.3 [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-c623d1e7a7524b76962806879cbfccc6
Source dataset
uspto-grants-2009_09
Patent number
US07582631B2

Reaction notes

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