Dichloromethane → HCID 178520177, compound

HRID 324568Notes

Reaction equation

HRID 324568 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11]([OH:13])=O)=[CH:9][C:4]=2[O:3][CH2:2]1.ClCCl.C1(N=C=NC2CCCCC2)CCCCC1.C(OC([N:39]1[C:43]([CH:44]2[CH2:46][CH2:45]2)=[CH:42][C:41]([NH2:47])=[N:40]1)=O)(C)(C)C>C(OCC)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11]([NH:47][C:41]3[NH:40][N:39]=[C:43]([CH:44]4[CH2:46][CH2:45]4)[CH:42]=3)=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 76115Benzo-1,3-dioxole-5-acetic acidHCID 11218347tert-butyl 3-amino-5-cyclopropyl-1H-pyrazole-1-carboxylate

Product 1

HCID 178520177HCID 178520177, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 96.8 mg (0.537 mmol) of 2-(1,3-benzodioxol-5-yl)-acetic acid in 3 ml of dichloromethane 360 mg (0.720 mmol) of polystyrene supported dicyclohexylcarbodiimide (loading=2 mmol/g) and 40 mg (0.179 mmol) of tert-butyl-3-amino-5-cyclopropyl-1H-pyrazole-1-carboxylate were added. The mixture was maintained under stirring at room temperature for 96 hours and after that time filtered, washed several times with dichloromethane and evaporated to dryness. The residue was re-dissolved with 3 ml of trifluoroacetic acid 10% V/V in dichloromethane and maintained at room temperature for an hour. The solvent was then evaporated, the residue re-dissolved in dichloromethane and washed with a saturated solution of sodium hydrogenocarbonate. The organic layer was evaporated to dryness to give, after trituration with diethylether, 32 mg (63% yield) of the title compound.

Workup

  1. additionwere added
  2. temperatureThe mixture was maintained
  3. filtrationafter that time filtered
  4. washwashed several times with dichloromethane
  5. customevaporated to dryness
  6. dissolutionThe residue was re-dissolved with 3 ml of trifluoroacetic acid 10% V/V in dichloromethane
  7. temperaturemaintained at room temperature for an hour
  8. customThe solvent was then evaporated
  9. dissolutionthe residue re-dissolved in dichloromethane
  10. washwashed with a saturated solution of sodium hydrogenocarbonate
  11. customThe organic layer was evaporated to dryness
  12. customto give

Sources & evidence

ORD record
ord-66b315f6301c4a5fa704f65c43232bb6
Source dataset
uspto-grants-2001_04
Patent number
US06218418B1

Reaction notes

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