Dimethylamine → HCID 68708005, compound

HRID 2097563Notes

Reaction equation

HRID 2097563 reaction equation
[CH3:1][N:2](C)[CH2:3]CCN=C=NCC.ON1C2C=CC=CC=2N=N1.CNC.[CH2:25]([O:27][C:28]1[CH:29]=[C:30]([C:37]2[S:38][CH:39]=[C:40]([CH2:42][CH2:43][C:44]([C:46]3[CH:54]=[CH:53][CH:52]=[CH:51][C:47]=3[C:48](O)=[O:49])=[O:45])[N:41]=2)[CH:31]=[CH:32][C:33]=1[O:34][CH2:35][CH3:36])[CH3:26]>CN(C=O)C.C(OCC)(=O)C.O>[CH2:25]([O:27][C:28]1[CH:29]=[C:30]([C:37]2[S:38][CH:39]=[C:40]([CH2:42][CH2:43][C:44]([C:46]3[CH:54]=[CH:53][CH:52]=[CH:51][C:47]=3[C:48]([N:2]([CH3:3])[CH3:1])=[O:49])=[O:45])[N:41]=2)[CH:31]=[CH:32][C:33]=1[O:34][CH2:35][CH3:36])[CH3:26]

Participants

8

Reactant 4

HCID 674DimethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 68708593HCID 68708593, compound

Product 1

HCID 68708005HCID 68708005, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (WSC) (54 mg, 0.29 mmol), 1-hydroxybenzotriazol (HOBT) (43 mg, 0.29 mmol), and a 50% aqueous dimethylamine solution (0.025 ml, 0.29 mmol) were added at room temperature to a solution (2 ml) of 2-{3-[2-(3,4-diethoxyphenyl)thiazole-4-yl]propionyl}benzoic acid (100 mg, 0.24 mmol) in DMF, followed by stirring at the same temperature for 2 hours. Water was added to the reaction mixture, and extraction with ethyl acetate was performed. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution, water and a saturated salt solution in this order, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3). The solvent was distilled off under reduced pressure, to thereby obtain 65 mg (yield: 61%) of 2-{3-[2-(3,4-diethoxyphenyl)thiazole-4-yl]propionyl}-N,N-dimethylbenzamide as a colorless oil.

Workup

  1. washThe organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution, water
  2. dry with materiala saturated salt solution in this order, and dried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3)
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3f71446d635b485c860477e1f65fede1
Source dataset
uspto-grants-2013_05
Patent number
US08450352B2

Reaction notes

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