Hydrochloric Acid → HCID 86613657, Verbindung

HRID 269284Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 269284
[F:1][C:2]([F:32])([F:31])[C:3]1[N:8]2[N:9]=[CH:10][C:11]([C:12]#[C:13][C:14]3[CH:15]=[CH:16][C:17]([NH2:20])=[N:18][CH:19]=3)=[C:7]2[N:6]=[C:5]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[CH:4]=1.[NH4+].[OH-].Cl.O.[C:37](OC(=O)C)(=[O:39])[CH3:38]>C1COCC1>[F:32][C:2]([F:1])([F:31])[C:3]1[N:8]2[N:9]=[CH:10][C:11]([C:12]#[C:13][C:14]3[CH:15]=[CH:16][C:17]([NH:20][C:37](=[O:39])[CH3:38])=[N:18][CH:19]=3)=[C:7]2[N:6]=[C:5]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:23][CH:22]=2)[CH:4]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 71533696Decoglurant

Produkt 1

HCID 86613657HCID 86613657, VerbindungAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 5-[7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidin-3-ylethynyl]-pyridin-2-ylamine (example 55) (2.00 g, 4.47 mmol) in acetic anhydride (15 mL) was stirred at 120° C. for 1 h. Cooled to 60° C., concentrated in vaccum to dryness (water bath temperature 60° C.) and dried in HV to give an orange solid (2.465 g, 113%, mixture of mono- and diacetylated compound). Suspended in THF (30 mL) at 23° C., added NH4OH (25%, 13.3M, 1.0 mL, 13.4 mmol) and stirred at 23° C. for 1.5 h resulting in a clear red solution, adjusted pH with 1N HCl until pH 1, added H2O (total volume 200 mL), filtered the precipitate off, washed with H2O and dried in HV, followed by trituration with ether and drying in HV to give the title compound as an orange solid (2.130 g, 97%). MS [ISN] 488.1[(M−H)−]; mp 266° C.

Aufarbeitung

  1. temperatureCooled to 60° C.
  2. concentrationconcentrated in vaccum to dryness (water bath temperature 60° C.)
  3. customdried in HV
  4. customto give
  5. additionan orange solid (2.465 g, 113%, mixture of mono- and diacetylated compound)
  6. stirringstirred at 23° C. for 1.5 h
  7. customresulting in a clear red solution
  8. filtrationfiltered the precipitate off,
  9. washwashed with H2O
  10. customdried in HV
  11. customdrying in HV

Quellen und Nachweise

ORD-Eintrag
ord-24754e42e56447dc9ec58fa2545206b9
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446113B2

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