N,N'-Dimethylethylenediamine → HCID 44155101, compound

HRID 2389276Notes

Reaction equation

HRID 2389276 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13](=[O:14])[NH:12][CH2:11][CH2:10][N:9]2[CH2:15][C:16]2[CH:17]=[C:18]([C:27]([O:29]CC)=[O:28])[C:19](=[O:26])[N:20]3[C:25]=2[CH:24]=[CH:23][CH:22]=[CH:21]3)[CH:5]=[CH:6][CH:7]=1.[C:32]1(I)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CNCCNC.C(=O)([O-])[O-].[Cs+].[Cs+]>[Cu]I>[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13](=[O:14])[N:12]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:11][CH2:10][N:9]2[CH2:15][C:16]2[CH:17]=[C:18]([C:27]([OH:29])=[O:28])[C:19](=[O:26])[N:20]3[C:25]=2[CH:24]=[CH:23][CH:22]=[CH:21]3)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 10796Cesium carbonateHCID 11575IodobenzeneHCID 58256235HCID 58256235, compound

Product 1

HCID 44155101HCID 44155101, compound

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 1-{[2-(3-fluorophenyl)-3-oxopiperazin-1-yl]methyl}-4-oxo-4 H-quinolizine-3-carboxylate (0.100 g, 0.236 mmol), phenyliodide (48.2 mg, 0.236 mmol), N,N′-dimethylethylenediamine (4.5 mg, 0.051 mmol), copper (I) iodide (4.5 mg, 0.024 mmol), and 1 N cesium carbonate (0.59 mL, 0.59 mmol) was heated under nitrogen to 100° C. for 18 hours. The reaction was then cooled to room temperature and concentrated in vacuo. The resultant residue was redissolved in 1 mL DMSO, and saturated aqueous LiOH (0.3 mL) was added. After 2 hours, the mixture was acidified with 6 N HCl to pH ˜3, filtered, and purified by reverse phase HPLC to provide the title compound which gave a proton NMR consistent with theory and a mass ion (ES+) of 471.9 for M+H+ [C27H22FN3O4: 471.48]: 1H NMR (400 MHz, DMSO-d6) δ 9.38 (d, J=7.2 Hz, 1H), 8.42 (s, 1H), 7.98-7.92 (m, 2H), 7.61-7.58 (m, 1H), 7.58-7.39 (m, 2H), 7.39-7.29 (m, 5H), 7.19 (d, J=9.8 Hz, 1H), 7.01-6.97 (m, 1H), 3.99 (s, 1H), 3.98-3.96 (m, 2H), 3.86 (d, J=13.5 Hz, 1H), 3.68-3.64 (m, 1H), 3.24-3.20 (m, 1H), 3.00-2.93 (m, 1H).

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. dissolutionThe resultant residue was redissolved in 1 mL DMSO
  4. additionsaturated aqueous LiOH (0.3 mL) was added
  5. filtrationfiltered
  6. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-c36e3e8d9b6547ab936f9df2bd7908a8
Source dataset
uspto-grants-2012_09
Patent number
US08273737B2

Reaction notes

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