Potassium Carbonate → HCID 86605637, compound

HRID 1986452Notes

Reaction equation

HRID 1986452 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=2)[N:11]=[C:10]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:9]=1[CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28].Cl[CH:33]([CH3:37])[C:34]([NH2:36])=[O:35].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:36][C:34](=[O:35])[CH:33]([CH3:37])[O:18][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:9]([CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[C:8]2[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 943852-ChloropropanamideHCID 86605636HCID 86605636, compound

Product 1

HCID 86605637HCID 86605637, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of tert-butyl [4-(2-fluorophenyl)-6-hydroxy-2-isobutylquinolin-3-yl]methylcarbamate (0.20 g, 0.47 mmol) and 2-chloropropionamide (0.076 g, 0.71 mmol) in N,N-dimethylformamide (20 ml) was added potassium carbonate (0.098 g, 0.71 mmol), and the mixture was stirred at 75° C. for 24 hrs. The reaction mixture was partitioned between ethyl acetate (100 ml) and 0.1N hydrochloric acid (150 ml). The aqueous layer was separated and extracted with ethyl acetate (100 ml). The organic layer and the extract were combined and the mixture was washed with saturated brine (100 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography and crystallized from diisopropyl ether-ethyl acetate to give tert-butyl [6-(2-amino-1-methyl-2-oxoethoxy)-4-(2-fluorophenyl)-2-isobutylquinolin-3-yl]methylcarbamate (0.15 g, yield 65%) as pale-yellow crystals.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (100 ml) and 0.1N hydrochloric acid (150 ml)
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (100 ml)
  4. washthe mixture was washed with saturated brine (100 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography
  8. customcrystallized from diisopropyl ether-ethyl acetate

Sources & evidence

ORD record
ord-9f77758255394ad7973d111938e690e3
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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