Dimethylamine → HCID 60143876, compound

HRID 337340Notes

Reaction equation

HRID 337340 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14](O)=[O:15])=[CH:10][C:9]=2[OH:17])[N:3]=1.Cl.[CH3:19][N:20](C)[CH2:21]CCN=C=NCC.ON1C2C=CC=CC=2N=N1.CNC>CN(C=O)C.O>[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([N:20]([CH3:21])[CH3:19])=[O:15])=[CH:10][C:9]=2[OH:17])[N:3]=1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 60143875HCID 60143875, compound

Product 1

HCID 60143876HCID 60143876, compoundYield 28.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

36 mg of 4-(3,5-dimethyl-1H-pyrazol-1-yl)-3-hydroxybenzene carboxylic acid was dissolved in 0.4 ml of DMF, and 36 mg of 1-(3-dimethylamino propyl)-3-ethylcarbodiimide hydrochloride, 25 mg of 1-hydroxybenzotriazole, and 93 μl of dimethylamine (2.0M THF solution) were added and stirred at room temperature for 4 hours. To the reaction mixture was added 10 ml of water, and extracted with 15 ml of ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and purified using a preparative thin-layer silica gel column chromatography (ethyl acetate) to yield 11.4 mg of the title compound.

Workup

  1. extractionextracted with 15 ml of ethyl acetate
  2. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. custompurified

Sources & evidence

ORD record
ord-4a93b1e89d2f4272abf70180dc969aad
Source dataset
uspto-grants-2014_11
Patent number
US08889727B2

Reaction notes

Loading…