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Isopropanol → HCID 56644307, Verbindung

HRID 2370973
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2370973
Cl.Cl[C:3]1[N:8]=[C:7]([NH:9][CH:10]2[CH2:15][C:14]([CH3:17])([CH3:16])[NH:13][C:12]([CH3:19])([CH3:18])[CH2:11]2)[C:6]([F:20])=[CH:5][N:4]=1.[CH:21]1([C:24]2[C:29]([N:30]3[C:34]([CH:35]([CH3:37])[CH3:36])=[N:33][N:32]=[N:31]3)=[CH:28][C:27]([NH2:38])=[C:26]([F:39])[CH:25]=2)[CH2:23][CH2:22]1.[CH:40]([OH:43])(C)C>>[NH3:4].[CH3:40][OH:43].[CH:21]1([C:24]2[C:29]([N:30]3[C:34]([CH:35]([CH3:37])[CH3:36])=[N:33][N:32]=[N:31]3)=[CH:28][C:27]([NH:38][C:3]3[N:8]=[C:7]([NH:9][CH:10]4[CH2:15][C:14]([CH3:17])([CH3:16])[NH:13][C:12]([CH3:19])([CH3:18])[CH2:11]4)[C:6]([F:20])=[CH:5][N:4]=3)=[C:26]([F:39])[CH:25]=2)[CH2:22][CH2:23]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 3776IsopropanolHCID 58065813HCID 58065813, VerbindungHCID 86653878HCID 86653878, Verbindung

Produkt 2

HCID 21705897Ammonia methanolAusbeute 1 %HCID 56644307HCID 56644307, VerbindungAusbeute 52 %

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 2-chloro-5-fluoro-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyrimidin-4-amine hydrochloride (300 mg, 0.928 mmol, 1 equiv), 4-cyclopropyl-2-fluoro-5-(5-isopropyl-1H-tetrazol-1-yl)benzenamine (291 mg, 1.11 mmol, 1.2 equiv), and PTSA monohydrate (191 mg, 0.742 mmol, 0.8 equiv) in isopropyl alcohol (10 mL) were heated to 70° C. for 7 days. After cooling to ambient temperature, the crude reaction mixture was concentrated to dryness and taken in water, EtOAc, and 1N NaOH. The layers were separated. The organic layer was washed with 1N NaOH 2×, dried over Na2SO4, filtered, and concentrated to dryness. The crude product was purified by flash chromatography and eluted with DCM:2M NH3/MeOH=100:0 to 96:4 using 1% 2M NH3/MeOH increments to give compound N2-(4-cyclopropyl-2-fluoro-5-(5-isopropyl-1H-tetrazol-1-yl)phenyl)-5-fluoro-N4-(2,2,6,6-tetramethylpiperidin-4-yl)pyrimidine-2,4-diamine (245 mg, 52%) as a solid.

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. customthe crude reaction mixture
  3. concentrationwas concentrated to dryness
  4. customThe layers were separated
  5. washThe organic layer was washed with 1N NaOH 2×
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe crude product was purified by flash chromatography
  10. washeluted with DCM

Quellen und Nachweise

ORD-Eintrag
ord-45c1deebde5d4dd19ce359bed23bcc68
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08710223B2

Notizen zur Reaktion

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