N,N-Dimethylethylenediamine → HCID 86634413, compound

HRID 1803065Notes

Reaction equation

HRID 1803065 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:6]=[CH:5]2.[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][NH2:26]>O1CCOCC1>[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][NH:26][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 685743166-Chloro-N-(2-phenoxyethyl)-2-quinolinamine

Product 1

HCID 86634413HCID 86634413, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

(6-Chloro-quinolin-2-yl)-(2-phenoxy-ethyl)-amine (100 mg, 0.33 mmol) was dissolved in 1.5 mL dioxane. Argon was bubbled through the solution for 2 minutes to remove oxygen. N,N-Dimethylethylendiamine (149 mg, 1.69 mmol), sodium tert.-butylate (80 mg, 0.83 mmol), 1,1′-bis(diphenylphosphin)ferrocen (21 mg, 0.037 mmol) and 1,1′-bis(diphenyl-phosphin)ferrocen-palladium(II)chloride (10 mg, 0.012 mmol) were added. The reaction mixture was stirred in a sealed tube at 120° C. overnight. The solvent was evaporated and the residue purified by flash chromatography on silica gel (dichloromethane/methanol 100:0→90:10 gradient). The title compound was obtained as a brown oil (35 mg, 30%), MS: m/e=351.3 (M+H+).

Workup

  1. customArgon was bubbled through the solution for 2 minutes
  2. customto remove oxygen
  3. customThe solvent was evaporated
  4. customthe residue purified by flash chromatography on silica gel (dichloromethane/methanol 100:0→90:10 gradient)

Sources & evidence

ORD record
ord-0684aea970c84dcfa5209c9e2c0e6eb1
Source dataset
uspto-grants-2013_01
Patent number
US08350028B2

Reaction notes

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