Ethylenediamine → HCID 67371795, compound

HRID 1753157Notes

Reaction equation

HRID 1753157 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][N:10]2[C:15](=[O:16])[CH:14]=[CH:13][CH:12]=[C:11]2[C:17]([OH:19])=O)=[CH:4][CH:3]=1.[CH2:21]([NH2:24])[CH2:22][NH2:23]>ClCCCl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]23[NH:24][CH2:21][CH2:22][N:23]2[C:17](=[O:19])[C:11]2[N:10]([C:15](=[O:16])[CH:14]=[CH:13][CH:12]=2)[CH2:9]3)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 67366489HCID 67366489, compound

Product 1

HCID 67371795HCID 67371795, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

To a suspension of 1-[2-(4-chlorophenyl)-2-oxoethyl]-6-oxo-1,6-dihydropyridine-2-carboxylic acid (50 mg, 0.17 mmol) in 1,2-dichloroethane (15 mL) was added ethane-1,2-diamine (0.1 mL, 1.5 mmol). The mixture was heated at reflux until completion (2 h, monitored by LMCS) and then diluted with water and extracted with CH2Cl2 (1×10 mL, 2×5 mL). The organic extracts were combined, dried (MgSO4), filtered and the filtrate concentrated in vacuo to yield a yellow oil that was purified by flash chromatography (Biotage SP4, 4 g cartridge, 0-10% MeOH gradient in CH2Cl2) to give 11a-(4-chlorophenyl)-2,3,11,11a-tetrahydro-1H-imidazo[1,2-a]pyrido[1,2-d]pyrazine-5,9-dione as a yellow oil (50 mg, yield 92%). 1H NMR (400 MHz, CDCl3): δ 1.73 (br s, 1H), 2.50 (br s, 1H), 2.89-3.02 (m, 1H), 3.33 (ddd, 1H, J 11.8, 7.5, 3.9 Hz), 3.50 (d, 1H, J 13.4 Hz), 3.59 (ddd, 1H, J 11.6, 7.5, 3.9 Hz), 3.97 (dt, 1H, J 11.4, 7.4 Hz), 5.55 (d, 1H, J 13.4 Hz), 6.60 (dd, 1H, J 9.2, 1.3 Hz), 7.07 (dd, 1H, J 6.8, 1.3 Hz), 7.22-7.28 (m, 4H), 7.34 (dd, 1H, J 9.2, 6.8 Hz).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux until completion (2 h, monitored by LMCS)
  3. extractionextracted with CH2Cl2 (1×10 mL, 2×5 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customto yield a yellow oil that
  8. customwas purified by flash chromatography (Biotage SP4, 4 g cartridge, 0-10% MeOH gradient in CH2Cl2)

Sources & evidence

ORD record
ord-3272ac95404149d49a601ad2e08a979a
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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