Pyridine → 2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-(5-tert-butyl-2H-pyrazol-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester

HRID 1446654Notes

Reaction equation

HRID 1446654 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH2:20])[N:8]([CH2:10][CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.Cl[C:28]([O:30][CH2:31][C:32]([Cl:35])([Cl:34])[Cl:33])=[O:29].C(OCC)(=O)C>C1COCC1.O>[Cl:33][C:32]([Cl:35])([Cl:34])[CH2:31][O:30][C:28](=[O:29])[NH:20][C:7]1[N:8]([CH2:10][CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:14])[CH3:15])[N:9]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 870632,2,2-Trichloroethyl chloroformateHCID 685465445-tert-Butyl-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2H-pyrazol-3-ylamine

Product 1

HCID 685422102-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-(5-tert-butyl-2H-pyrazol-3-yl)-carbamic acid 2,2,2-trichloro-ethyl esterYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 5-tert-butyl-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2H-pyrazol-3-ylamine (5.5 g, 0.018 mol) in THF (100 mL) under N2 and cool to 0° C. Add pyridine (1.6 mL, 1.1 equiv.) via syringe followed by dropwise addition of 2,2,2-trichloroethyl chloroformate (2.7 mL, 1.1 equiv.). Stir the reaction at 0° C. for one hour then remove the cooling bath and allow the reaction to stir for a total of 5 hours. Dilute the reaction with ethyl acetate and water. Wash the organic layer with water then saturated aqueous saturated sodium chloride and then dry over magnesium sulfate, filter, and concentrate in vacuo to give a residue (8.7 g, 100%) that is used without further purification. MS (ES), m/z 474 (M+1).

Workup

  1. customthe reaction at 0° C. for one hour
  2. customthen remove the cooling bath
  3. customthe reaction
  4. stirringto stir for a total of 5 hours
  5. additionDilute
  6. washWash the organic layer with water
  7. dry with materialsaturated aqueous saturated sodium chloride and then dry over magnesium sulfate
  8. filtrationfilter
  9. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-1cc696cb95e44dee9e7e38a7c65012dd
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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