Diisopropylethylamine → N-(3-tert-butylphenyl)-4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

HRID 216038

Reaktionsgleichung

Reaktionsgleichung von HRID 216038
[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([C:14]2([CH3:20])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[O:13])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:22]1[C:23]2[C:30]([CH3:31])=[CH:29][NH:28][C:24]=2[N:25]=[CH:26][N:27]=1.C(N(CC)C(C)C)(C)C>C(O)(C)C>[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([C:14]2([CH3:20])[CH2:15][CH2:16][N:17]([C:22]3[C:23]4[C:30]([CH3:31])=[CH:29][NH:28][C:24]=4[N:25]=[CH:26][N:27]=3)[CH2:18][CH2:19]2)=[O:13])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 148092824-Chloro-5-methyl-7H-pyrrolo(2,3-d)pyrimidineHCID 67036907N-(3-tert-butylphenyl)-4-methylpiperidine-4-carboxamide

Produkt 1

HCID 57920200N-(3-tert-butylphenyl)-4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamideAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

N-(3-tert-Butylphenyl)-4-methylpiperidine-4-carboxamide from step B (0.33 g, 1.07 mmol), 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (0.18 g, 1.07 mmol), N,N-diisopropylethylamine (0.69 g. 5.34 mmol), and isopropanol (7 mL) were combined in a pressure rated sealed tube and heated at 100° C. for 18 hours. The mixture was concentrated and taken up in dichloromethane from which a precipitate (0.18 g) was collected. The solution was chromatographed (SiO2, 0-2% MeOH:CH2Cl2), and the columned material (0.15 g) was combined with the precipitate and dissolved in methanol (15 mL) at 60° C. Water was added (5.0 mL), and the mixture was cooled. The resultant precipitate was filtered, washed with water, and dried to give the title compound in 50% yield.

Aufarbeitung

  1. customrated sealed tube
  2. concentrationThe mixture was concentrated
  3. customwas collected
  4. customThe solution was chromatographed (SiO2, 0-2% MeOH:CH2Cl2)
  5. dissolutiondissolved in methanol (15 mL) at 60° C
  6. additionWater was added (5.0 mL)
  7. temperaturethe mixture was cooled
  8. filtrationThe resultant precipitate was filtered
  9. washwashed with water
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e15e43a43d3d432fb844832efe67b292
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193202B2

Verknüpfte Notizen

Wird geladen…