Pyridine → [5-(1-Fluoromethyl-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloro-ethyl ester

HRID 1993679Notes

Reaction equation

HRID 1993679 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])=[O:3].[F:10][CH2:11][C:12]1([C:15]2[CH:16]=[C:17]([NH2:27])[N:18]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)[N:19]=2)[CH2:14][CH2:13]1.N1C=CC=CC=1.CCOC(C)=O>C1COCC1>[Cl:7][C:6]([Cl:9])([Cl:8])[CH2:5][O:4][C:2](=[O:3])[NH:27][C:17]1[N:18]([C:20]2[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=2)[N:19]=[C:15]([C:12]2([CH2:11][F:10])[CH2:13][CH2:14]2)[CH:16]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 870632,2,2-Trichloroethyl chloroformateHCID 685381145-(1-fluoromethyl-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-ylamine

Product 1

HCID 68538084[5-(1-Fluoromethyl-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloro-ethyl esterYield 36.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Slowly add ClCO2CH2CCl3 (1.00 equiv; 717.49 μmoles; 152.01 mg) to a solution of 5-(1-fluoromethyl-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-ylamine (176 mg, 0.71 mmoles) and pyridine in 4 mL of THF under nitrogen at 0° C. Stir the mixture from 0° C. to room temperature for 5 hours. Filter the insoluble and remove solvent from filtrate under reduced pressure give an oil. Subject oil to chromatorgraphy (hex/AcOEt 20-80%) to give 110 mg of title compound as a yellow oil. MS (ES+): m/z=420.0 [M+H].

Workup

  1. customat 0° C
  2. filtrationFilter the insoluble and
  3. customremove solvent from filtrate under reduced pressure
  4. customgive an oil

Sources & evidence

ORD record
ord-b045f703638345acbc03b9864b96e4fe
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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