Hydrochloric Acid → HCID 68828771, compound

HRID 1986465Notes

Reaction equation

HRID 1986465 reaction equation
[NH2:1][C:2]([C:4]1[O:8][C:7]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[C:14]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:13]([CH2:23][NH:24]C(=O)OC(C)(C)C)=[C:12]3[C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)=[CH:6][CH:5]=1)=[O:3].Cl>C(OCC)(=O)C>[NH2:24][CH2:23][C:13]1[C:14]([CH2:19][CH:20]([CH3:22])[CH3:21])=[N:15][C:16]2[C:11]([C:12]=1[C:32]1[CH:33]=[CH:34][C:35]([CH3:38])=[CH:36][CH:37]=1)=[CH:10][C:9]([C:7]1[O:8][C:4]([C:2]([NH2:1])=[O:3])=[CH:5][CH:6]=1)=[CH:18][CH:17]=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86605643HCID 86605643, compound

Product 1

HCID 68828771HCID 68828771, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of tert-butyl {[6-[5-(aminocarbonyl)-2-furyl]-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate (0.5 g, 1.0 mmol) in ethyl acetate (5 ml) was added 4N solution of hydrogen chloride in ethyl acetate (2 ml), and the mixture was stirred at room temperature for 3 hrs. The reaction mixture was concentrated under reduced pressure and the residue was crystallized from diisopropyl ether. The obtained crystals were dissolved in ethyl acetate (5 ml) and triethylamine (1 ml) was added. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from diisopropyl ether to give 5-[3-(aminomethyl)-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]-2-furamide (0.29 g, yield 71%) as white crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was crystallized from diisopropyl ether
  3. dissolutionThe obtained crystals were dissolved in ethyl acetate (5 ml)
  4. additiontriethylamine (1 ml) was added
  5. additionWater was added to the reaction mixture
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-9054fdaf537748608ba821e9fcadf469
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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