tert-Butanol → HCID 58563674, Verbindung

HRID 241944Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 241944
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][N:4]2[N:8]=[C:9](C(O)=O)[CH:10]=[C:3]12.C([N:16]([CH2:19]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.[C:38]([OH:42])([CH3:41])([CH3:40])[CH3:39]>C1(C)C=CC=CC=1>[C:38]([O:42][C:19](=[O:28])[NH:16][C:9]1[CH:10]=[C:3]2[C:2](=[O:1])[CH2:7][CH2:6][CH2:5][N:4]2[N:8]=1)([CH3:41])([CH3:40])[CH3:39]

Komponenten

6

Edukt 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 226053224-oxo-4H,5H,6H,7H-pyrazolo[1,5-a]pyridine-2- carboxylic acid

Produkt 1

HCID 58563674HCID 58563674, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 4-oxo-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyridine-2-carboxylic acid (2.56 g, 14.2 mmol, prepared according to EP1241170) in 160 mL dry toluene is added triethylamine (2.38 mL, 17.1 mmol) and diphenylphosphoryl azide (3.68 mL, 17.1 mmol) and the reaction mixture is stirred overnight at RT. Then tert-butanol (26.7 mL, 74.1 mmol) is added and the reaction is heated to 120° C. for 5 h. The solvents are removed under reduced pressure and the residue is purified by flash column chromatography (silica gel, 0-70% ethyl acetate in cyclohexane). Yield: 2.32 g. HPLC-MS: Rt=1.55 min, (M+H-56)+=196. 1H NMR (DMSO-d6): δ 9.8 (s, 1H), 6.7 (s, 1H), 4.2 (t, 2H), 2.6 (t, 2H), 2.3 (quint, 2H), 1.4 (s, 9H).

Aufarbeitung

  1. temperaturethe reaction is heated to 120° C. for 5 h
  2. customThe solvents are removed under reduced pressure
  3. customthe residue is purified by flash column chromatography (silica gel, 0-70% ethyl acetate in cyclohexane)

Quellen und Nachweise

ORD-Eintrag
ord-8fc1b93c6591466885934fcbc3b18f93
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653097B2

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