Imidazole → (5-Imidazol-1-yl-thiophen-3-yl)-(octahydro-quinolin-1-yl)-methanone

HRID 2068613Notes

Reaction equation

HRID 2068613 reaction equation
Br[C:2]1[S:6][CH:5]=[C:4]([C:7]([N:9]2[C@@H:18]3[C@@H:13]([CH2:14][CH2:15][CH2:16][CH2:17]3)[CH2:12][CH2:11][CH2:10]2)=[O:8])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C[NH:26][CH2:27][CH2:28][NH:29][CH3:30].N1C=CN=C1>COCCOC.C(Cl)Cl.[Cu]I>[N:26]1([C:2]2[S:6][CH:5]=[C:4]([C:7]([N:9]3[CH:18]4[CH:13]([CH2:14][CH2:15][CH2:16][CH2:17]4)[CH2:12][CH2:11][CH2:10]3)=[O:8])[CH:3]=2)[CH:27]=[CH:28][N:29]=[CH:30]1

Participants

8

Reactant 4

HCID 795ImidazoleHCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 86646712HCID 86646712, compound

Product 1

HCID 44224463(5-Imidazol-1-yl-thiophen-3-yl)-(octahydro-quinolin-1-yl)-methanoneYield 274.8%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

cis-(5-Bromo-thiophen-3-yl)-(octahydro-quinolin-1-yl)-methanone (0.15 mmol) was added to a solution of potassium carbonate (0.15 mmol), N,N′-dimethylethylene-diamine (0.03 mmol), imidazole (0.3 mmol) and copper (I) iodide (0.03 mmol) in DME (1 mL). The reaction mixture was heated under nitrogen to 120° C. for 90 hours and then diluted with DCM (5 mL) and washed with water. The organic solution was dried and filtered and the solvent evaporated. The residue was purified by HPLC, eluting with 10%-98% acetonitrile in water (0.1% formic acid) over 30 minutes. The fractions containing the desired product were concentrated under vacuum to give the title compound as a pale brown solid (26 mg). LCMS m/z 316.06 [M+H]+ RT=6.44 min. (Analytical Method 2).

Workup

  1. washwashed with water
  2. customThe organic solution was dried
  3. filtrationfiltered
  4. customthe solvent evaporated
  5. customThe residue was purified by HPLC
  6. washeluting with 10%-98% acetonitrile in water (0.1% formic acid) over 30 minutes
  7. additionThe fractions containing the desired product
  8. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-ce5cd0c0457a40aea963f69ade052cb8
Source dataset
uspto-grants-2012_10
Patent number
US08299063B2

Reaction notes

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