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Isopropanol → 4-(4-Chloro-5-(2,5-dimethyl-7-(pentan-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)thiazol-2-yl)morpholine

HRID 1044665
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1044665
[CH2:1]([CH:3]([C:6]1[N:11]2[N:12]=[C:13]([CH3:22])[C:14]([C:15]3[S:19][C:18](Cl)=[N:17][C:16]=3[Cl:21])=[C:10]2[N:9]=[C:8]([CH3:23])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].CC(O)C.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>O>[CH2:1]([CH:3]([C:6]1[N:11]2[N:12]=[C:13]([CH3:22])[C:14]([C:15]3[S:19][C:18]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[N:17][C:16]=3[Cl:21])=[C:10]2[N:9]=[C:8]([CH3:23])[CH:7]=1)[CH2:4][CH3:5])[CH3:2]
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Komponenten

5

Edukt 3

HCID 3776Isopropanol2×HCID 8083MorpholineHCID 452757037-(1-Ethyl-propyl)-3-(2,4-dichloro-thiazol-5-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine

Produkt 1

HCID 248989774-(4-Chloro-5-(2,5-dimethyl-7-(pentan-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)thiazol-2-yl)morpholineAusbeute 94,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

7-(1-ethyl-propyl)-3-(2,4-dichloro-thiazol-5-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine (11.64 mmoles) is charged into a 100 mL 3-necked round bottomed flask followed by addition of 2-propanol (16 mL, 3.72 volumes). The yellowish brown slurry is stirred at about 20° C. for 5 min. Then morpholine (3.3 g, 37.84 mmoles) is added over 2-5 minutes. Contents are refluxed for 6 hr. The slurry is cooled to 25° C. 2-Propanol (32 mL, 7.44 volumes) and water (8.6 mL, 2.0 volumes) are added and the mixture warmed to 70-75° C., filtered and concentrated to ˜9 volumes at atmospheric pressure. The clear solution is gradually cooled to 55° C., seeded with 0.06 g of crystalline 7-(1-ethyl-propyl)-3-(4-chloro-2-morpholin-4-yl-thiazol-5-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine slurried in 0.5 mL 2-propanol, rinsed with additional 0.5 mL 2-propanol and added to crystallization flask. The slurry is cooled to 0-5° C., maintained for 1 hr., filtered and the product rinsed with 2-propanol (9 mL, 2.1 volumes). Suctioned dried under vacuum at 60° C. to afford 4.6 g of dry 7-(1-ethyl-propyl)-3-(4-chloro-2-morpholin-4-yl-thiazol-5-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine (88.8% yield, purity by HPLC assay is 99.88%). MS (ES)=420 (M+1).

Aufarbeitung

  1. temperatureContents are refluxed for 6 hr
  2. temperatureThe slurry is cooled to 25° C
  3. temperaturethe mixture warmed to 70-75° C.
  4. filtrationfiltered
  5. concentrationconcentrated to ˜9 volumes at atmospheric pressure
  6. temperatureThe clear solution is gradually cooled to 55° C.
  7. washrinsed with additional 0.5 mL 2-propanol
  8. additionadded to crystallization flask
  9. temperatureThe slurry is cooled to 0-5° C.
  10. temperaturemaintained for 1 hr
  11. filtration, filtered
  12. washthe product rinsed with 2-propanol (9 mL, 2.1 volumes)
  13. customSuctioned dried under vacuum at 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-8a0e97fbab7f47e28ff734da8ab6a728
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08563718B2

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