Pyridine → HCID 67063093, Verbindung

HRID 599338Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 599338
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.Cl[C:24]([O:26][C:27]([CH3:29])=[CH2:28])=[O:25]>C(Cl)Cl>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:24](=[O:25])[O:26][C:27]([CH3:29])=[CH2:28])[N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 93846Isopropenyl chloroformateHCID 7706343-tert-butyl-1-phenyl-1H-pyrazol-5-amine

Produkt 1

HCID 67063093HCID 67063093, VerbindungAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of Example B1 (10.00 g, 46.4 mmol, 1.00 eq) and pyridine (7.58 ml, 92.9 mmol, 2.00 eq) in CH2Cl2 (225 ml) at 0° C. was added isopropenyl chloroformate (5.33 ml, 4.8.8 mol, 1.05 eq). After 45 min at 0° C., the completed reaction was washed with 3M HCl (2×), satd. NaHCO3 (1×), and brine (1×), dried (MgSO4), filtered and evaporated to afford crude product (14.9 g) as an oil that solidified on the pump. The crude material obtained was upgraded by triturating in warm (60° C.) hexanes (70 ml) for 20-30 min until a powdery precipitate was obtained. After cooling to RT, the solids were collected by filtration, rinsing forward with hexanes. The cake was washed with more hexanes and then dried on the filter to afford prop-1-en-2-yl 3-t-butyl-1-phenyl-1H-pyrazol-5-ylcarbamate (10.79 g, 78% yield) as a tan powder which was used as is in the next reaction. MS (ESI) m/z: 300.3 (M+H+).

Aufarbeitung

  1. customthe completed reaction
  2. washwas washed with 3M HCl (2×)
  3. dry with materialNaHCO3 (1×), and brine (1×), dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto afford crude product (14.9 g) as an oil that
  7. customThe crude material obtained
  8. customby triturating
  9. customwas obtained
  10. temperatureAfter cooling to RT
  11. filtrationthe solids were collected by filtration
  12. washrinsing forward with hexanes
  13. washThe cake was washed with more hexanes
  14. customdried on the
  15. filtrationfilter

Quellen und Nachweise

ORD-Eintrag
ord-1d819bbe5efa4e69bd34496d4da6b945
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897762B2

Notizen zur Reaktion

Wird geladen…