1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-[(1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carbonyl)amino]propionic acid

HRID 632936Notes

Reaction equation

HRID 632936 reaction equation
[C:1]1([N:7]2[CH:11]=[C:10]([C:12]([OH:14])=O)[C:9]([C:15]([F:18])([F:17])[F:16])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN=C=NCCCN(C)C.[NH2:30][CH2:31][CH2:32][C:33]([O:35]C)=[O:34].C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)C(C)C)C>ClCCl.C([O-])(O)=O.[Na+]>[C:1]1([N:7]2[CH:11]=[C:10]([C:12]([NH:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[O:14])[C:9]([C:15]([F:18])([F:17])[F:16])=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 192794Methyl beta-alanateHCID 149682451-Phenyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid

Product 1

HCID 1179202273-[(1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carbonyl)amino]propionic acidYield 97%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (150 mg, 0.57 mmol), EDCI (280.6 mg, 1.5 mmol), methyl 3-aminopropionate (163.5 mg, 1.17 mmol), HOBt (118.7 mg, 0.8 mmol) and ethyldiisopropylamine (265.5 mg, 2.1 mmol) dissolved in dichloromethane (15 mL) were stirred for 24 hours. The reaction mixture was diluted with aqueous NaHCO3 and extracted with dichloromethane. The extract was washed with brine and dried with anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica gel column chromatography to obtain the desired compound (181 mg, 91%) as a white solid.

Workup

  1. extractionextracted with dichloromethane
  2. washThe extract was washed with brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-168b819ab40a490cbb40d097e76c9ea1
Source dataset
uspto-grants-2016_04
Patent number
US09321728B2

Reaction notes

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