Potassium Carbonate → HCID 21094414, compound

HRID 1350175Notes

Reaction equation

HRID 1350175 reaction equation
[CH2:1]([C@@H:3]1[CH2:24][O:23][C:6]2=[C:7]3[C:12](=[CH:13][CH:14]=[C:5]2[NH:4]1)[N:11]=[C:10]([O:15][CH:16]([CH3:18])[CH3:17])[CH:9]=[C:8]3[C:19]([F:22])([F:21])[F:20])[CH3:2].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([C@@H:3]1[CH2:24][O:23][C:6]2=[C:7]3[C:12](=[CH:13][CH:14]=[C:5]2[N:4]1[CH2:8][C:7]([CH3:12])=[CH2:6])[N:11]=[C:10]([O:15][CH:16]([CH3:18])[CH3:17])[CH:9]=[C:8]3[C:19]([F:21])([F:22])[F:20])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 69319657HCID 69319657, compound

Product 1

HCID 21094414HCID 21094414, compoundYield 171.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

This compound was prepared by treatment of (3R)-3-ethyl-3,4-dihydro-8-isopropoxy-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline (20 mg, 0.059 mmol), 2-methallyl bromide (40 mg, 0.30 mmol) and K2CO3 (41 mg, 0.30 mmol) in 1 mL DMF heated at 50° C. for 16 h. The reaction was treated with an additional 2-methallyl bromide (60 mg) and was heated overnight at 50° C. The mixture was extracted with ethyl acetate (2×25 mL), and the combined organic layers were washed with water (25 mL), brine (25 mL), dried over MgSO4, filtered, and concentrated afford 20 mg (87%) of (3R)-3-ethyl-4-(2-methyl-2-propenyl)-3,4-dihydro-8-isopropoxy-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline after flash chromatography (9:1 hexanes:EtOAc). 1H NMR (400 MHz, CDCl3) δ7.39 (d, J=9.0, 1H), 7.18 (s, 1H), 7.12 (d, J=9.0, 1H), 5.47 (septet, J=6.2, 1H), 4.91 (broad s, 2H), 4.33 (dd, J=10.7, 2.1, 1H), 3.96 (dd, J=10.7, 2.6, 1H), 3.85 (d, AB, J=17.1, 1H), 3.80 (d, AB, J=17.1, 1H), 3.20–3.26 (m, 1H), 1.79 (s, 3H), 1.58–1.68 (m, 2H), 1.38 (d, J=6.2, 3H), 1.37 (d, J=6.2, 3H), 0.96 (t, J=7.4, 3H).

Workup

  1. temperaturewas heated overnight at 50° C
  2. extractionThe mixture was extracted with ethyl acetate (2×25 mL)
  3. washthe combined organic layers were washed with water (25 mL), brine (25 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-65b9615eb9d74107af3a430f2fccd060
Source dataset
uspto-grants-2007_05
Patent number
US07214690B2

Reaction notes

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