Dimethylamine → HCID 86723878, compound

HRID 576773Notes

Reaction equation

HRID 576773 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[C:19](=[O:20])[N:18]([CH2:21][CH2:22][C:23](O)=[O:24])[C:17](=[O:26])[N:16]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=4)[C:15]=3[CH3:37])=[CH:12][CH:11]=[N:10]2)=[CH:5][CH:4]=1)#[N:2].[CH2:38]([N:40]=[C:41]=NCCCN(C)C)C.ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.CNC.S([O-])(O)(=O)=O.[K+]>O1CCCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:13]([C:14]3[C:19](=[O:20])[N:18]([CH2:21][CH2:22][C:23]([N:40]([CH3:41])[CH3:38])=[O:24])[C:17](=[O:26])[N:16]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:34])([F:36])[F:35])[CH:28]=4)[C:15]=3[CH3:37])=[CH:12][CH:11]=[N:10]2)=[CH:7][CH:8]=1)#[N:2]

Participants

8

Reactant 6

HCID 674DimethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 516920Potassium bisulfateHCID 86723876HCID 86723876, compound

Product 1

HCID 86723878HCID 86723878, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[5-[1-(4-cyanophenyl)-1H-pyrazol-5-yl]-4-methyl-2,6-dioxo-3-(3-trifluoromethylphenyl)-2,3-dihydropyrimidin-1(6H)-yl]propanoic acid (prepared in Example 73) (26.4 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (13.8 mg), 1-hydroxy-7-azabenzotriazole (15.9 mg) and N,N-diisopropylethylamine (0.1 ml) in tetrahydrofuran (0.5 ml) was cooled under ice-cooling and thereto was added dimethylamine (0.05 ml: 2M tetrahydrofuran solution) and the resulting mixture was stirred at room temperature for five hours. To the reaction mixture was 1M aqueous potassium hydrogen sulfate solution (20 ml) and the resulting mixture was then extracted with ethyl acetate (20 ml×2). The organic layer was washed with water (10 ml) and saturated saline (20 ml), dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol) to afford 3-[5-[1-(4-cyanophenyl)-1H-pyrazole-5-yl]-4-methyl-2,6-dioxo-3-(3-trifluoromethylphenyl)-2,3-dihydropyrimidin-1(6H)-yl]-N,N-dimethylpropaneamide (3.1 mg).

Workup

  1. temperaturecooling
  2. extractionthe resulting mixture was then extracted with ethyl acetate (20 ml×2)
  3. washThe organic layer was washed with water (10 ml) and saturated saline (20 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol)

Sources & evidence

ORD record
ord-5ba8f6fec4194ccd96ca1684da3bd769
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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