HCID 89183463, compound → HCID 66697344, compound

HRID 877015Notes

Reaction equation

HRID 877015 reaction equation
[CH2:1]([C:4]1[C:12]2[C:11](=[O:13])[N:10]([CH3:14])[C:9](=[O:15])[N:8]([CH3:16])[C:7]=2[S:6][C:5]=1C(O)=O)[CH:2]=[CH2:3]>N1C2C(=CC=CC=2)C=CC=1.C(OCC)(=O)C.[Cu]>[CH2:1]([C:4]1[C:12]2[C:11](=[O:13])[N:10]([CH3:14])[C:9](=[O:15])[N:8]([CH3:16])[C:7]=2[S:6][CH:5]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 1

HCID 89183463HCID 89183463, compound

Product 1

HCID 66697344HCID 66697344, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 7047QuinolineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
235 °C

Procedure

Copper powder (231 mg, 3.642 g atom) was added to a suspension of Step 7 intermediate (3.4 g, 12.142 mmol) in quinoline (60 ml) and the resulting mixture was stirred and heated at 235° C. for 3 h under nitrogen. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, washed with 1 N HCl and water. The combined organic layers were dried and concentrated. The purification of crude product by silica gel column chromatography by using 5% ethyl acetate in petroleum ether gave 2.17 g of the product as an off-white solid; 1H NMR (300 MHz, CDCl3) δ 3.41 (s, 3H), 3.55 (s, 3H), 3.71 (s, 2H), 5.09-5.15 (m, 2H), 5.97-6.10 (m, 1H), 6.50 (s, 1H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with 1 N HCl and water
  3. customThe combined organic layers were dried
  4. concentrationconcentrated
  5. customThe purification of crude product by silica gel column chromatography

Sources & evidence

ORD record
ord-63a5949c62e2479ca4633de669dea819
Source dataset
uspto-grants-2015_03
Patent number
US08987278B2

Reaction notes

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