Hydrochloric Acid → HCID 86669272, compound

HRID 2366930Notes

Reaction equation

HRID 2366930 reaction equation
[CH3:1][CH:2]([O:4][C:5](=[O:35])[NH:6][C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[N:21]=[C:20]([CH2:22][NH:23]C(OC(C)(C)C)=O)[O:19][N:18]=3)[CH:15]=2)[N:10]([C:31](=[O:33])[CH3:32])[C@@H:9]([CH3:34])[CH2:8]1)[CH3:3].[ClH:36].CCOCC>O1CCOCC1>[ClH:36].[C:31]([N:10]1[C:11]2[C:16](=[CH:15][C:14]([C:17]3[N:21]=[C:20]([CH2:22][NH2:23])[O:19][N:18]=3)=[CH:13][CH:12]=2)[C@H:7]([NH:6][C:5](=[O:35])[O:4][CH:2]([CH3:1])[CH3:3])[CH2:8][C@@H:9]1[CH3:34])(=[O:33])[CH3:32]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 68187780HCID 68187780, compound

Product 1

HCID 86669272HCID 86669272, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-methylethyl((2S,4R)-1-acetyl-6-{5-[({[(1,1-dimethylethyl)oxy]carbonyl}amino)methyl]-1,2,4-oxadiazol-3-yl}-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate (for a preparation, see Intermediate 60) (132 mg, 0.271 mmol) in 1,4-dioxane (2 mL) at room temperature was added HCl (4N in 1,4-dioxane, 2 mL, 8.00 mmol) and the resulting mixture was stirred at this temperature for 5 h then left standing at 4° C. for 16 h. The mixture was warmed to room temperature and most of the solvent was removed in vacuo. The residue was loaded on a 2 G SCX cartridge and eluted with MeOH then with a 2N NH3 solution in MeOH. The ammonia fractions were collected and concentrated in vacuo, The residue was dissolved in 1,4-dioxane (3 mL) and the solution was treated with 0.5 ml of HCl (4N in 1,4-dioxane) then concentrated in vacuo. Trituration of the residue with Et2O gave 1-methylethyl {(2S,4R)-1-acetyl-6-[5-(aminomethyl)-1,2,4-oxadiazol-3-yl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate hydrochloride (71 mg, 0.167 mmol, 61.9% yield) as a pale red solid.

Workup

  1. customat room temperature
  2. waitthen left
  3. waitstanding at 4° C. for 16 h
  4. customwas removed in vacuo
  5. washeluted with MeOH
  6. customThe ammonia fractions were collected
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue was dissolved in 1,4-dioxane (3 mL)
  9. additionthe solution was treated with 0.5 ml of HCl (4N in 1,4-dioxane)
  10. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-226df9ece1e240f19dfb1ea617ef76cb
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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