Sodium Carbonate → 6-(3-{2-tert-Butyl-6-oxo-4H,5H,6H-thieno[2,3-c]pyrrol-5-yl}-2-methylphenyl)-4-({5-methyl-4H,5H,6H,7H-pyrazolo[1,5-a]pyrazin-2-yl}amino)-2,3-dihydropyridazin-3-one

HRID 872144Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 872144
Cl[C:2]1[CH:3]=[C:4]([NH:9][C:10]2[CH:19]=[C:13]3[CH2:14][N:15]([CH3:18])[CH2:16][CH2:17][N:12]3[N:11]=2)[C:5](=[O:8])[NH:6][N:7]=1.[C:20]([C:24]1[S:31][C:30]2[C:29](=[O:32])[N:28]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35](B4OC(C)(C)C(C)(C)O4)[C:34]=3[CH3:48])[CH2:27][C:26]=2[CH:25]=1)([CH3:23])([CH3:22])[CH3:21].O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.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>[C:20]([C:24]1[S:31][C:30]2[C:29](=[O:32])[N:28]([C:33]3[C:34]([CH3:48])=[C:35]([C:2]4[CH:3]=[C:4]([NH:9][C:10]5[CH:19]=[C:13]6[CH2:14][N:15]([CH3:18])[CH2:16][CH2:17][N:12]6[N:11]=5)[C:5](=[O:8])[NH:6][N:7]=4)[CH:36]=[CH:37][CH:38]=3)[CH2:27][C:26]=2[CH:25]=1)([CH3:23])([CH3:21])[CH3:22]

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 585403166-chloro-4-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)pyridazin-3(2H)-oneHCID 898241832-tert-Butyl-5-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4H-thieno[3,2-c]pyrrol-6(5H)-one

Produkt 1

HCID 569290576-(3-{2-tert-Butyl-6-oxo-4H,5H,6H-thieno[2,3-c]pyrrol-5-yl}-2-methylphenyl)-4-({5-methyl-4H,5H,6H,7H-pyrazolo[1,5-a]pyrazin-2-yl}amino)-2,3-dihydropyridazin-3-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In a dried pressure flask was placed 0.968 mmol of 101m, 1.065 mmol of 101g, and 56 mg (5 mol %) of tetrakis(triphenylphosphine)palladium(0), The flask was evacuated under vacuum, then filled with nitrogen. This procedure was repeated twice more, then 8 mL of anhydrous dioxane and 2.4 mL (2.5 equivalents) of 1 M aqueous sodium carbonate solution were added, and the mixture was heated at 100° for 18 h. The mixture was cooled to room temperature, then diluted with ethyl acetate, washed with saturated aqueous saturated NaCl solution four times, dried over anhydrous Na2SO4, and purified by chromatography on a Biotage 25M KP NH column to afford 101. 1H NMR (400 MHz, DMSO) δ 12.96 (s, 1H), 9.19 (s, 1H), 7.78 (s, 1H), 7.54-7.32 (m, 3H), 7.15 (s, 1H), 5.97 (s, 1H), 4.78 (s, 2H), 3.97 (t, J=5.3, 2H), 3.52 (s, 2H), 2.80 (t, J=5.4, 2H), 2.36 (s, 3H), 2.11 (d, J=12.1, 3H), 1.42 (s, 9H). ESIMS m/z=530.2 (M+1).

Aufarbeitung

  1. customIn a dried pressure flask was placed
  2. additionfilled with nitrogen
  3. temperaturethe mixture was heated at 100° for 18 h
  4. washwashed with saturated aqueous saturated NaCl solution four times
  5. dry with materialdried over anhydrous Na2SO4
  6. custompurified by chromatography on a Biotage 25M KP NH column

Quellen und Nachweise

ORD-Eintrag
ord-b1e6ed06ec934978bfc3d6affc003907
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975260B2

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