Potassium Carbonate → HCID 86679183, compound

HRID 1774831Notes

Reaction equation

HRID 1774831 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH3:19])[C:14](=[O:20])[CH2:13][CH2:12]3)[CH:6]=[N:7][CH:8]=1.C([O-])([O-])=O.[K+].[K+].[CH2:27]([C:29]1([NH2:33])[CH2:32][O:31][CH2:30]1)[CH3:28]>CN(C=O)C>[CH2:27]([C:29]1([NH:33][CH2:2][C:3]2[CH:4]=[C:5]([C:9]3[CH:10]=[C:11]4[C:16](=[CH:17][CH:18]=3)[N:15]([CH3:19])[C:14](=[O:20])[CH2:13][CH2:12]4)[CH:6]=[N:7][CH:8]=2)[CH2:32][O:31][CH2:30]1)[CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 72207351HCID 72207351, compoundHCID 86679182HCID 86679182, compound

Product 1

HCID 86679183HCID 86679183, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-(5-chloromethyl-pyridin-3-yl)-1-methyl-3,4-dihydro-1H-quinolin-2-one (190 mg, 0.66 mmol) in DMF (5.0 mL) was added K2CO3 (276 mg, 2.0 mmol) and 3-ethyl-oxetan-3-ylamine (415 mg, 3.0 mmol) at room temperature and the resulting reaction mixture was stirred at room temperature for additional 12 hours. After extraction with EtOAc, the organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a crude product which was purified by prep-HPLC to give title compound (35 mg, 17.2%) as a light yellow solid. MS: 352.1 (M+H+).

Workup

  1. customthe resulting reaction mixture
  2. extractionAfter extraction with EtOAc
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a crude product which
  8. customwas purified by prep-HPLC

Sources & evidence

ORD record
ord-5ab72f9a3e344b78b4607ee51ca27f63
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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