6-Formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile → HCID 178458708, Verbindung

HRID 968716Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 968716
[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][NH:5][C:6]1[S:7][CH2:8][C:9](=[O:11])[N:10]=1.C(O[Na])(C)=O.[CH:21]([C:23]1[N:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[N:29]=[CH:28][C:27]([C:33]#[N:34])=[C:26]2[O:35][CH:36]([CH3:38])[CH3:37])=O>CC(O)=O>[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][NH:5][C:6]1[S:7][C:8](=[CH:21][C:23]2[N:24]=[C:25]3[C:30](=[CH:31][CH:32]=2)[N:29]=[CH:28][C:27]([C:33]#[N:34])=[C:26]3[O:35][CH:36]([CH3:38])[CH3:37])[C:9](=[O:11])[N:10]=1

Komponenten

5

Edukt 3

HCID 587243116-Formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrileHCID 178418247HCID 178418247, VerbindungHCID 178516939HCID 178516939, Verbindung

Produkt 1

HCID 178458708HCID 178458708, VerbindungAusbeute 35,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a mixture of 2-(2-chloro-benzylamino)-thiazol-4-one (48.1 mg, 0.20 mmol) (prepared as described below), AcONa (160 mg, 1.95 mmol), molecular sieves, and 6-formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile (53.1 mg, 0.22 mmol, (see Example 1) in a sealed tube was added AcOH (0.3 mL). The reaction mixture was heated to 85-95° C. (oil bath) for 1.5 h. The reaction mixture was then cooled to r.t. and triturated with water. The solid was collected by filtration and washed with water. The solid was then suspended in hot MeOH (50 mL) and filtered again. The filtrate was concentrated to give a brown solid: 120.3 mg, which was purified by Biotage flash column (1%-6% MeOH in CH2Cl2) to give 6-[2-(2-chloro-benzylamino)-4-oxo-4H-thiazol-5-ylidenemethyl]-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile as a yellowish solid (32.8 mg, 35.3%). HR-ES (+) m/e calcd for C23H18ClN5O2S (M+H)+ 464.0943. found 464.0943.

Aufarbeitung

  1. temperatureThe reaction mixture was then cooled to r.t.
  2. customtriturated with water
  3. filtrationThe solid was collected by filtration
  4. washwashed with water
  5. filtrationfiltered again
  6. concentrationThe filtrate was concentrated
  7. customto give a brown solid
  8. custom120.3 mg, which was purified by Biotage flash column (1%-6% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-eb66941ec13442abb2a65e69639bf8ea
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07304074B2

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