N,N'-Dimethylethylenediamine → HCID 178464139, compound

HRID 1170444Notes

Reaction equation

HRID 1170444 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([O:34][Si](CC)(CC)CC)[C:17]2[C:12](=[CH:13][C:14](I)=[CH:15][C:16]=2[C:18]([F:21])([F:20])[F:19])[N:11]([CH2:23][C@H:24]2[CH2:27][C@H:26]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[CH2:25]2)[C:10]1=[O:33].[NH:42]1[CH:46]=[CH:45][N:44]=[N:43]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>CN(C)C=O.[Cu](I)I.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([OH:34])[C:17]2[C:12](=[CH:13][C:14]([N:42]3[CH:46]=[CH:45][N:44]=[N:43]3)=[CH:15][C:16]=2[C:18]([F:21])([F:20])[F:19])[N:11]([CH2:23][C@H:24]2[CH2:25][C@H:26]([N:28]([CH2:29][CH3:30])[CH2:31][CH3:32])[CH2:27]2)[C:10]1=[O:33]

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 178418936HCID 178418936, compoundHCID 178464149HCID 178464149, compound

Product 1

HCID 178464139HCID 178464139, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of the compound of Example 14-1 (75 mg, 0.101 mmol) in N,N-dimethylformamide (1 mL) were added triazole (7.0 mg, 0.101 mmol), potassium phosphate (43 mg, 0.202 mmol), N,N′-dimethylethylenediamine (15 mg, 0.170 mmol) and copper iodide (1) (1.0 mg, 0.01 mmol) under nitrogen, and the mixture was stirred at 100° C. for 8 hours. To the reaction solution was added water, and the mixture was extracted with ethyl acetate, and then the organic layer was washed with saturated saline, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography (chloroform/methanol/28% ammonia water=100/5/1) to give the titled compound (20 mg, 63%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with saturated saline
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel chromatography (chloroform/methanol/28% ammonia water=100/5/1)

Sources & evidence

ORD record
ord-a1379e3b8038478eb49d00c813522182
Source dataset
uspto-grants-2010_11
Patent number
US07825155B2

Reaction notes

Loading…