N,N'-Dimethylethylenediamine → HCID 123141395, compound

HRID 1893612Notes

Reaction equation

HRID 1893612 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][N:2]1[N:10]([CH3:39])[C:11](=[O:38])[CH2:12][N:13]([C:30]1[CH:35]=[CH:34][C:33](I)=[CH:32][C:31]=1[CH3:37])[CH2:14][C:15]([NH:17][CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH3:22])=[O:16].[NH:40]1[CH2:44][CH2:43][CH2:42][C:41]1=[O:45].CNCCNC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][N:2]1[N:10]([CH3:39])[C:11](=[O:38])[CH2:12][N:13]([C:30]1[CH:35]=[CH:34][C:33]([N:40]2[CH2:44][CH2:43][CH2:42][C:41]2=[O:45])=[CH:32][C:31]=1[CH3:37])[CH2:14][C:15]([NH:17][CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH3:22])=[O:16]

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 120252-PyrrolidoneHCID 62657Potassium Phosphate, TribasicHCID 123606779HCID 123606779, compound

Product 1

HCID 123141395HCID 123141395, compoundYield 89.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound (650 mg, 1.00 mmol) of Example 293, step A, 2-pyrrolidone (128 mg, 1.50 mmol), copper iodide(I) (19 mg, 0.10 mmol), N,N′-dimethylethylenediamine (0.022 ml, 0.20 mmol) and potassium phosphate (425 mg, 2.00 mmol) were dissolved in toluene (4.0 ml), and the mixture was heated under reflux for 7 hr. The reaction mixture was diluted with ethyl acetate and water, and the organic layer was extracted. The organic layer was washed with saturated brine and dried over sodium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane) to give the title compound (542 mg, yield 89%) as a brown oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 7 hr
  3. extractionthe organic layer was extracted
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe solution was concentrated under reduced pressure
  8. customThe obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-1ad1d2c1dafc48f781bb2071322228a4
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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