3-(Tributylstannanyl)pyridazine → 5-[2-(4-Cyclobutylpiperazin-1-Yl)-2-Oxoethyl]-2-Pyridazin-3-Yl-4,5,6,7-Tetrahydro[1,3]Thiazolo[5,4-C]Pyridine

HRID 1713157Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1713157
Br[C:2]1[S:3][C:4]2[CH2:5][N:6]([CH2:11][C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH:20]4[CH2:23][CH2:22][CH2:21]4)[CH2:16][CH2:15]3)=[O:13])[CH2:7][CH2:8][C:9]=2[N:10]=1.C([Sn](CCCC)(CCCC)[C:29]1[N:30]=[N:31][CH:32]=[CH:33][CH:34]=1)CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:20]1([N:17]2[CH2:18][CH2:19][N:14]([C:12](=[O:13])[CH2:11][N:6]3[CH2:7][CH2:8][C:9]4[N:10]=[C:2]([C:29]5[N:30]=[N:31][CH:32]=[CH:33][CH:34]=5)[S:3][C:4]=4[CH2:5]3)[CH2:15][CH2:16]2)[CH2:23][CH2:22][CH2:21]1

Komponenten

5

Edukt 2

HCID 27632603-(Tributylstannanyl)pyridazineHCID 574205862-Bromo-5-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine

Produkt 1

HCID 574207635-[2-(4-Cyclobutylpiperazin-1-Yl)-2-Oxoethyl]-2-Pyridazin-3-Yl-4,5,6,7-Tetrahydro[1,3]Thiazolo[5,4-C]Pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 2-bromo-5-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine (300 mg, 0.75 mmol), 3-(tributylstannyl)pyridazine (369 mg, 1 mmol) and Pd(PPh3)4 (92 mg, 0.08 mmol) in toluene (15 mL) is degassed by Ar and heated at 110° C. in a sealed tube overnight. The mixture is cooled and saturated KF solution (10 mL) is added. The mixture is stirred at rt for 30 min then the layers are separated. The aqueous layer is extracted with EtOAc (15 ml) and the combined extracts are dried and evaporated. The residue is purified by PTLC to give the title compound as white solid. MS (M+1): 399.2; 1H NMR (δ, CDCl3): 9.63-9.64 (m, 1H), 9.23 (dd, 1H), 7.84 (dd, 1H), 3.90 (s, 2H), 3.62 (td, 4H), 3.45 (s, 2H), 3.00 (s, 4H), 2.64-2.74 (m, 1H), 2.29 (t, 4H), 1.64-2.06 (m, 6H).

Aufarbeitung

  1. customis degassed by Ar
  2. temperatureThe mixture is cooled
  3. additionsaturated KF solution (10 mL) is added
  4. customthe layers are separated
  5. extractionThe aqueous layer is extracted with EtOAc (15 ml)
  6. customthe combined extracts are dried
  7. customevaporated
  8. customThe residue is purified by PTLC

Quellen und Nachweise

ORD-Eintrag
ord-3ab5a6f2906844f1acd0b80e8b705bf8
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795262B2

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