Dimethylformamide → HCID 178483899, compound

HRID 1294831Notes

Reaction equation

HRID 1294831 reaction equation
[H-].[Na+].[CH:3]1([O:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH:19]=[CH:18][N:17]([C@H:20]4[CH2:25][CH2:24][C@H:23]([OH:26])[CH2:22][CH2:21]4)[C:16]3=[O:27])=[CH:11][CH:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1.CN(C=O)C.[CH3:33][N:34]([CH2:36][CH2:37]Cl)[CH3:35]>O>[CH:3]1([O:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH:19]=[CH:18][N:17]([C@H:20]4[CH2:25][CH2:24][C@H:23]([O:26][CH2:37][CH2:36][N:34]([CH3:35])[CH3:33])[CH2:22][CH2:21]4)[C:16]3=[O:27])=[CH:11][CH:10]=2)[CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 178517285HCID 178517285, compound

Product 1

HCID 178483899HCID 178483899, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (42 mg) was added to a mixture of trans-1-(4-cyclopentyloxy-phenyl)-3-(4-hydroxycyclohexyl)-1,3-dihydroimidazol-2-one (0.30 g) and DMF (10 ml) and, after gas evolution ceased, dimethylaminoethyl chloride (94 mg) was added. After eight hours, the reaction solution was diluted with water, and the mixture was extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and concentrated. The residue was purified by preparative HPLC. The product with the molecular weight of 413.56 (C24H35N3O3) was obtained in this way; MS (ESI): 414 ([M+H]+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC
  6. customThe product with the molecular weight of 413.56 (C24H35N3O3) was obtained in this way

Sources & evidence

ORD record
ord-c81372de590744739a3b6c5588907680
Source dataset
uspto-grants-2007_07
Patent number
US07241787B2

Reaction notes

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