Ethylenediamine → HCID 67608732, compound

HRID 2401518Notes

Reaction equation

HRID 2401518 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]2[C:11]([C:16]([OH:18])=O)=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:4][CH:3]=1.[CH2:20]([NH2:23])[CH2:21][NH2:22]>ClCCCl.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]23[NH:23][CH2:20][CH2:21][N:22]2[C:16](=[O:18])[C:11]2[N:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9]3)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 67606381HCID 67606381, compound

Product 1

HCID 67608732HCID 67608732, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Procedure

To a suspension of 3-[2-(4-fluorophenyl)-2-oxoethyl]pyridine-2-carboxylic acid (1.5 g, 5.8 mmol) in 1,2-dichloroethane (100 mL) was added ethylenediamine (8 mL, 120 mmol) and the resulting solution heated at reflux for 1 hour. The resulting suspension was then allowed to cool to room temperature before being concentrated in vacuo to yield a thick, orange gum. The gum was suspended in methanol with the aid of sonication and filtered. The filtrate was adsorbed onto silica and purified by flash chromatography (5 to 7.5% methanol-dichloromethane) to yield 10a-(4-fluorophenyl)-2,3,10,10a-tetrahydroimidazo[2,1-g][1,7]naphthyridin-5(1H)-one as a pale yellow solid (1.1 g, 67% yield). ESI-MI m/z [M+H]+ 284.04. 1H NMR (400 MHz, CDCl3) δ 8.66 (brd, J=4.7 Hz, 1H), 7.36 (brd, J=7.7 Hz, 1H), 7.30 (dd, J=8.9, 5.2 Hz, 2H), 7.23 (dd, J=7.7, 4.7 Hz, 1H), 6.89 (t, J=8.7 Hz, 2H), 4.02-3.89 (m, 1H), 3.70-3.60 (m, 1H), 3.47 (d, J=15.2 Hz, 1H), 3.42 (d, J=15.2 Hz, 1H), 3.35 (ddd, J=12.4, 7.9, 2.8 Hz, 1H), 2.86-2.74 (m, 1H), 2.49 (brs, 1H).

Workup

  1. temperaturethe resulting solution heated
  2. temperatureat reflux for 1 hour
  3. concentrationbefore being concentrated in vacuo
  4. customto yield a thick, orange gum
  5. filtrationfiltered
  6. custompurified by flash chromatography (5 to 7.5% methanol-dichloromethane)

Sources & evidence

ORD record
ord-bdbd2e2c01db4ece987967f5315f7a3c
Source dataset
uspto-grants-2014_08
Patent number
US08796303B2

Reaction notes

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