1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86721240, compound

HRID 1750396Notes

Reaction equation

HRID 1750396 reaction equation
[Br:1][C:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:5]=[CH:4][C:3]=1[C:11]([OH:13])=O.CC[N:16]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl-].[NH4+]>CN(C=O)C>[Br:1][C:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:5]=[CH:4][C:3]=1[C:11]([NH2:16])=[O:13]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 8613611098534-79-3

Product 1

HCID 86721240HCID 86721240, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the compound (10.29 g, 41.64 mmol) obtained in step 3, WSC (9.58 g, 49.97 mmol), HOBt (6.75 g, 49.97 mmol), TEA (6.97 ml, 49.97 mmol) and ammonium chloride (2.67 g, 49.97 mmol) in DMF (100 mL) was stirred at room temperature for 14 hr. The reaction mixture was concentrated under reduced pressure, and water and ethyl acetate were added to the residue. The organic layer was washed with water, aqueous sodium hydrogen carbonate solution and saturated brine and dried, and the solvent was evaporated under reduced pressure to give 5-bromo-1-tert-butyl-1H-pyrazole-4-carboxamide (6.18 g, 25.1 mmol, 60%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and water and ethyl acetate
  2. additionwere added to the residue
  3. washThe organic layer was washed with water, aqueous sodium hydrogen carbonate solution and saturated brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ea380e68f08b49088017fcebde91740a
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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