N,N-Dimethylglycine → 2-Dimethylamino-N-{4-[2-oxo-3-(4-phenoxyphenyl)-2,3-dihydroimidazol-1-yl]phenyl}acetamide

HRID 723374Notes

Reaction equation

HRID 723374 reaction equation
[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[NH2:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH:34]=[CH:33][N:32]([C:35]3[CH:40]=[CH:39][C:38]([O:41][C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)=[CH:37][CH:36]=3)[C:31]2=[O:48])=[CH:26][CH:25]=1.CCN(C(C)C)C(C)C.[CH3:58][N:59]([CH3:64])[CH2:60][C:61](O)=[O:62]>CN(C=O)C.O>[CH3:58][N:59]([CH3:64])[CH2:60][C:61]([NH:23][C:24]1[CH:25]=[CH:26][C:27]([N:30]2[CH:34]=[CH:33][N:32]([C:35]3[CH:40]=[CH:39][C:38]([O:41][C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)=[CH:37][CH:36]=3)[C:31]2=[O:48])=[CH:28][CH:29]=1)=[O:62]

Participants

7

Reactant 4

HCID 673N,N-DimethylglycineHCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 102468281-(4-Aminophenyl)-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one

Product 1

HCID 218734972-Dimethylamino-N-{4-[2-oxo-3-(4-phenoxyphenyl)-2,3-dihydroimidazol-1-yl]phenyl}acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

TOTU (327 mg) was added to a solution of 1-(4-aminophenyl)-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one (343 mg) in DMF (3 ml) at 0° C. After 10 minutes, Hünig base (130 mg) and then a solution of dimethylglycine (103 mg) in DMF (1 ml) was added. After a reaction time of 12 hours at room temperature, the mixture was mixed with water and extracted with ethyl acetate. The organic phase was washed with sodium bicarbonate solution, dried over magnesium sulfate and concentrated. The residue was purified by preparative HPLC. The product with the molecular weight of 428.50 (C25H24N4O3); MS (ESI): 429 ([M+H]+) was obtained as hydrotrifluoroacetate in this way.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC
  6. customMS (ESI): 429 ([M+H]+) was obtained as hydrotrifluoroacetate in this way

Sources & evidence

ORD record
ord-2ec5c750372743508bfd8f7ef27ffb95
Source dataset
uspto-grants-2006_11
Patent number
US07141561B2

Reaction notes

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