Triethylamine → 2-[5-(4-Chlorophenyl)-1-(4-methoxyphenyl)-3-pyrazolyl]-ethylamine

HRID 373495Notes

Reaction equation

HRID 373495 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[N:11]=[C:10]([CH2:21][CH2:22]C(O)=O)[CH:9]=2)=[CH:4][CH:3]=1.CC[N:28](CC)CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[N:11]=[C:10]([CH2:21][CH2:22][NH2:28])[CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1888503-[5-(4-chlorophenyl)-1-(4-methoxyphenyl)pyrazol-3-yl]propanoic AcidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 144975792-[5-(4-Chlorophenyl)-1-(4-methoxyphenyl)-3-pyrazolyl]-ethylamine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of the acid 12 (1.0 g, 2.8 mM) in benzene (25 ml) was added Et3N (0.39 ml, 2.8 mM) and diphenylphosphoryl azide (0.60 ml, 2.8 mM). After stirring overnight at room temperature, the reaction mixture was heated to 70° C. for 1.5 hours, cooled and concentrated in vacuo. Dioxane (2 ml), followed by a solution of concentrated HCl (0.3 ml) in dioxane (2 ml) was added, and the reaction mixture was heated to reflux for 2 hours, cooled and diluted to 50 ml with EtOAc. The organic solution was washed with a 0.25N NaOH solution, and extracted with 1N HCl. The extracts were combined, basified with 5N NaOH, and extracted with EtOAc, dried, filtered and concentrated in vacuo. Crystallization from Et2O afforded pure 42 (0.62 g, 68%) as a light yellow crystalline solid, mp=95°-97°. MS, m/e 327 (M+).

Workup

  1. temperaturethe reaction mixture was heated to 70° C. for 1.5 hours
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. additionwas added
  5. temperaturethe reaction mixture was heated
  6. temperatureto reflux for 2 hours
  7. temperaturecooled
  8. additiondiluted to 50 ml with EtOAc
  9. washThe organic solution was washed with a 0.25N NaOH solution
  10. extractionextracted with 1N HCl
  11. extractionextracted with EtOAc
  12. customdried
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo
  15. customCrystallization from Et2O afforded pure 42 (0.62 g, 68%) as a light yellow crystalline solid, mp=95°-97°

Sources & evidence

ORD record
ord-eacdb49e9a0246048bd884c2be364982
Source dataset
uspto-grants-1992_11
Patent number
US05164381

Reaction notes

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