1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86721219, compound

HRID 1750379Notes

Reaction equation

HRID 1750379 reaction equation
[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[C:8]([C:18]([OH:20])=O)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:22][NH:23][O:24][CH3:25].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.O>[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[C:8]([C:18]([N:23]([O:24][CH3:25])[CH3:22])=[O:20])[CH:7]=[N:6]1)([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 86721218HCID 86721218, compound

Product 1

HCID 86721219HCID 86721219, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of the compound (300 mg, 1.09 mmol) obtained in step 2, N,O-dimethylhydroxylamine monohydrochloride (160 mg, 1.64 mmol), HOBt (222 mg, 1.64 mmol), WSC (314 mg, 1.64 mmol) and TEA (0.228 mL, 1.64 mmol) in DMF (5 mL) was stirred at room temperature for 3 days. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and aqueous sodium hydrogen carbonate solution and dried, and the solvent was evaporated under reduced pressure to give a crude product 1-tert-butyl-N-methoxy-5-(4-methoxyphenyl)-N-methyl-1H-pyrazole-4-carboxamide (320 mg, 1.008 mmol, 92%) as a pale-yellow powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and aqueous sodium hydrogen carbonate solution
  3. customdried
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f8f327a5eb194ffcbe1baf15a589013a
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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