Potassium Carbonate → HCID 9800002, compound

HRID 1744569Notes

Reaction equation

HRID 1744569 reaction equation
[F:1][C:2]([F:13])([F:12])[CH2:3][N:4]1[CH:8]=[C:7]([C:9]([OH:11])=O)[CH:6]=[N:5]1.[NH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:23][CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[C:19]([CH:22]=1)[C:20]#[N:21].ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:20]([C:19]1[CH:22]=[C:15]([NH:14][C:9]([C:7]2[CH:6]=[N:5][N:4]([CH2:3][C:2]([F:1])([F:13])[F:12])[CH:8]=2)=[O:11])[CH:16]=[CH:17][C:18]=1[O:23][CH2:24][C:25]([CH3:27])([CH3:26])[CH3:28])#[N:21]

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 164908041-(2,2,2-Trifluoroethyl)-1H-pyrazole-4-carboxylic acidHCID 178227345-Amino-2-neopentyloxybenzonitrile

Product 1

HCID 9800002HCID 9800002, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(2,2,2-Trifluoroethyl)pyrazole-4-carboxylic acid (2.2 g), 5-amino-2-neopentyloxybenzonitrile (2.5 g), 1-hydroxybenzotriazole (1.8 g) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (2.6 g) were added to dimethylformamide (20 ml) and the mixture was stirred at room temperature for 1.5 h. The reaction mixture was treated with aqueous potassium carbonate solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to allow crystallization. The crystals were recrystallized from ethyl acetate to give the title compound (1.8 g), melting point 159–160° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customafter which the solvent was evaporated under reduced pressure
  5. additionDiisopropyl ether was added to the residue
  6. customcrystallization
  7. customThe crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c9a6161d4ee34c2c8572690badaedc97
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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