Diisopropylethylamine → HCID 86687067, Verbindung

HRID 1402213Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1402213
Cl[C:2]1[N:6]2[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.Cl.[OH:13][C@H:14]1[CH2:19][CH2:18][CH2:17][NH:16][CH2:15]1.CCN(C(C)C)C(C)C>CC(N(C)C)=O>[F:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([N:16]3[CH2:17][CH2:18][CH2:19][C@H:14]([OH:13])[CH2:15]3)=[N:3][N:4]=2)[CH:7]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 16211918(3S)-Piperidin-3-ol--hydrogen chloride (1/1)HCID 552675403-Chloro-6-fluoro-[1,2,4]triazolo[4,3-a]pyridine

Produkt 1

HCID 86687067HCID 86687067, VerbindungAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
175 °C

Versuchsvorschrift

A mixture of Intermediate 24b (394 mg, 2.30 mmol), (S)-3-hydroxypiperidine hydrochloride (1.00 g, 7.27 mmol) and DIPEA (1.27 mL, 7.30 mmol) in DMA (8 mL) was heated in the microwave at 170-180° C. for 9.5 h. The cooled mixture was concentrated in vacuo and applied to an SCX-2 cartridge (70 g), washing with methanol then eluting basic components with 0.4-2 M ammonia in methanol. Product containing fractions were combined and concentrated in vacuo. The residue was purified by FCC, using 0-20% MeOH in DCM, to give the title compound as a pale brown solid (204 mg, 38%). LCMS (Method 3): Rt 2.02 min, m/z 237 [MH+].

Aufarbeitung

  1. concentrationThe cooled mixture was concentrated in vacuo
  2. washwashing with methanol
  3. washthen eluting basic components with 0.4-2 M ammonia in methanol
  4. additionProduct containing fractions
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by FCC

Quellen und Nachweise

ORD-Eintrag
ord-fc3cee5646f54168a028084f5c1f0d26
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08907094B2

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