Hydrochloric Acid → HCID 68833761, compound

HRID 1986453Notes

Reaction equation

HRID 1986453 reaction equation
[NH2:1][C:2](=[O:36])[CH:3]([CH3:35])[O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:9]([CH2:19][NH:20]C(=O)OC(C)(C)C)=[C:8]2[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[F:34].Cl>O1CCOCC1>[NH2:20][CH2:19][C:9]1[C:10]([CH2:15][CH:16]([CH3:18])[CH3:17])=[N:11][C:12]2[C:7]([C:8]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[F:34])=[CH:6][C:5]([O:4][CH:3]([CH3:35])[C:2]([NH2:1])=[O:36])=[CH:14][CH:13]=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86605637HCID 86605637, compound

Product 1

HCID 68833761HCID 68833761, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To tert-butyl [6-(2-amino-1-methyl-2-oxoethoxy)-4-(2-fluorophenyl)-2-isobutylquinolin-3-yl]methylcarbamate (0.12 g, 0.24 mmol) was added 4N solution of hydrogen chloride in 1,4-dioxane (5 ml) and the mixture was stirred at room temperature for 30 min. The reaction mixture was partitioned between ethyl acetate-isopropanol (4:1, 125 ml) and 10% aqueous potassium carbonate solution (100 ml). The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (0.070 g, yield 73%) as a colorless powder.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate-isopropanol (4:1, 125 ml) and 10% aqueous potassium carbonate solution (100 ml)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-44fdf279257b4f43b660d8a63d5e1c77
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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