Triethylamine → HCID 18707306, compound

HRID 1421980Notes

Reaction equation

HRID 1421980 reaction equation
[CH2:1]([N:3](CC)[CH2:4]C)C.[CH2:8]([O:10][C:11]1[CH:12]=[C:13]([C:20]2[S:21][CH:22]=[C:23]([C:25]3[N:30]=[C:29]([C:31](O)=[O:32])[CH:28]=[CH:27][CH:26]=3)[N:24]=2)[CH:14]=[CH:15][C:16]=1[O:17][CH2:18][CH3:19])[CH3:9].Cl.CNC.P(C#N)(OCC)(OCC)=O>CN(C)C=O.O>[CH2:8]([O:10][C:11]1[CH:12]=[C:13]([C:20]2[S:21][CH:22]=[C:23]([C:25]3[N:30]=[C:29]([C:31]([N:3]([CH3:4])[CH3:1])=[O:32])[CH:28]=[CH:27][CH:26]=3)[N:24]=2)[CH:14]=[CH:15][C:16]=1[O:17][CH2:18][CH3:19])[CH3:9]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 76257Diethyl cyanophosphonateHCID 3025803Tetomilast

Product 1

HCID 18707306HCID 18707306, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1.13 ml of triethylamine was dropwise added, at room temperature, to a solution of 1 g of 2-(3,4-diethoxyphenyl)-4-(2-carboxy-6-pyridyl)thiazole, 245 mg of dimethylamine hydrochloride and 515 mg of diethyl cyanophosphate in 15 ml of dimethylformamide. The mixture was stirred at the same temperature for 3 hours. The reaction mixture was mixed with 20 ml of water. The resulting mixture was extracted with 50 ml of dichloromethane three times. The dichloromethane layer was dried over sodium sulfate and concentrated. The residue was recrystallized from n-hexane-ethyl acetate-dichloromethane to obtain 800 mg of 2-(3,4-diethoxyphenyl)-4-(2-dimethylaminocarbonyl-6-pyridyl)thiazole.

Workup

  1. extractionThe resulting mixture was extracted with 50 ml of dichloromethane three times
  2. dry with materialThe dichloromethane layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was recrystallized from n-hexane-ethyl acetate-dichloromethane

Sources & evidence

ORD record
ord-9cbd79285beb4a8eb83aa72c9ada2bde
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Reaction notes

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