Diphenylacetic Acid → N-(5-cyclopropyl-1-terbutoxycarbonyl-pyrazol-3-yl)-2,2-diphenyl acetamide

HRID 324567Notes

Reaction equation

HRID 324567 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.CN(C)CCCN=C=NCC.[C:29]([O:33][C:34]([N:36]1[C:40]([CH:41]2[CH2:43][CH2:42]2)=[CH:39][C:38]([NH2:44])=[N:37]1)=[O:35])([CH3:32])([CH3:31])[CH3:30]>ClCCl>[CH:41]1([C:40]2[N:36]([C:34]([O:33][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:35])[N:37]=[C:38]([NH:44][C:8](=[O:10])[CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:39]=2)[CH2:42][CH2:43]1

Participants

5

Reactant 3

HCID 8333Diphenylacetic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11218347tert-butyl 3-amino-5-cyclopropyl-1H-pyrazole-1-carboxylate

Product 1

HCID 11418646N-(5-cyclopropyl-1-terbutoxycarbonyl-pyrazol-3-yl)-2,2-diphenyl acetamideYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 45.6 mg (0.215 mmol) of diphenylacetic acid in 3 ml of dichloromethane at 0° C. 41.2 mg (0.215 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride were added. After 1 hour at the same temperature under stirring 40 mg (0.179 mmol) of tert-butyl-3-amino-5-cyclopropyl-1H-pyrazole-1-carboxylate were added. The mixture was maintained at room temperature for 16 hours, then was diluted with dichloromethane and washed with a saturated solution of sodium hydrogenocarbonate. The organic layer was dried over anhydrous sodium sulfate evaporated to dryness, to give, after column chromatography (hexane-ethylacetate) 60 mg (80% yield) of N-(5-cyclopropyl-1-terbutoxycarbonyl-pyrazol-3-yl)-2,2-diphenyl acetamide. This intermediate was submitted to hydrolysis with 15 ml of trifluoroacetic acid 10% v/v in dichloromethane for an hour. The solvent was then evaporated under vacuum. the residue redissolved with dichloromethane and washed with a saturated solution sodium hydrogen carbonate. The organic layer was dried over anhydrous sodium sulfate and evaporated to give 42 mg (92% yield) of the title compound.

Workup

  1. customat 0° C
  2. additionwere added
  3. washwashed with a saturated solution of sodium hydrogenocarbonate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customevaporated to dryness
  6. customto give

Sources & evidence

ORD record
ord-6223f3c4c4434e6aaf00eb0752f14a09
Source dataset
uspto-grants-2001_04
Patent number
US06218418B1

Reaction notes

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