HCID 86605659, compound → HCID 68829553, compound

HRID 1986490Notes

Reaction equation

HRID 1986490 reaction equation
[NH2:1][C:2](=[O:37])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:11]([CH2:21][NH:22]C(=O)OC(C)(C)C)=[C:10]2[C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=1>FC(F)(F)C(O)=O>[NH2:22][CH2:21][C:11]1[C:12]([CH2:17][CH:18]([CH3:20])[CH3:19])=[N:13][C:14]2[C:9]([C:10]=1[C:30]1[CH:31]=[CH:32][C:33]([CH3:36])=[CH:34][CH:35]=1)=[CH:8][C:7]([O:6][CH2:5][CH2:4][CH2:3][C:2]([NH2:1])=[O:37])=[CH:16][CH:15]=2

Participants

3

Reactant 1

HCID 86605659HCID 86605659, compound

Product 1

HCID 68829553HCID 68829553, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl {[6-(4-amino-4-oxobutoxy)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate (0.5 g, 0.99 mmol) in trifluoroacetic acid (10 ml) was stirred at 0° C. for 3 hrs. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in ethyl acetate. The obtained-solution was washed twice with saturated aqueous sodium hydrogen carbonate, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from diethyl ether to give the title compound (0.25 g, yield 63%) as crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe obtained-solution was washed twice with saturated aqueous sodium hydrogen carbonate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-9a2126d97a91412480a0888d0915fe88
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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