Cesium carbonate → 6-{4-[4-(5-Chloro-1H-indole-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-phenyl}-2-(2-morpholin-4-yl-ethyl)-2H-pyridazin-3-one

HRID 28401Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 28401
Cl.Cl[C:3]1[CH:4]=[CH:5][C:6](=[O:17])[N:7]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[N:8]=1.[Cl:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23]([S:28]([N:31]1[CH2:36][CH2:35][N:34]([C:37]([C:39]3[CH:44]=[CH:43][C:42](B(O)O)=[CH:41][CH:40]=3)=O)[CH2:33][CH2:32]1)(=[O:30])=[O:29])=[CH:22]2.C(=O)([O-])[O-:49].[Cs+].[Cs+]>CC(N(C)C)=O.O.C(O)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23]([S:28]([N:31]1[CH2:32][CH2:33][N:34]([CH2:37][C:39]3[CH:44]=[CH:43][C:42]([C:3]4[CH:4]=[CH:5][C:6](=[O:17])[N:7]([CH2:9][CH2:10][N:11]5[CH2:16][CH2:15][O:14][CH2:13][CH2:12]5)[N:8]=4)=[CH:41][CH:40]=3)[C:35](=[O:49])[CH2:36]1)(=[O:30])=[O:29])=[CH:22]2

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 693065846-Chloro-2-(2-morpholin-4-yl-ethyl)-2H-pyridazin-3-one hydrochlorideHCID 693073894-({4-[(5-chloro-1H-indol-2-yl)sulphonyl]piperazin-1-yl}carbonyl)phenyl boronic acid

Produkt 1

HCID 117633996-{4-[4-(5-Chloro-1H-indole-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-phenyl}-2-(2-morpholin-4-yl-ethyl)-2H-pyridazin-3-oneAusbeute 68,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 131727010Dimethyl acetamide water ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

6-Chloro-2-(2-morpholin-4-yl-ethyl)-2H-pyridazin-3-one hydrochloride, (63 mg, 0.22 mmol), 4-({4-[(5-chloro-1H-indol-2-yl)sulphonyl]piperazin-1-yl}carbonyl)-phenyl boronic acid (78 mg, 0.17 mmol), caesium carbonate (156 mg, 0.48 mmol), and bis(triphenylphosphine) palladium (II) chloride (11 mg, 0.02 mmol,) were mixed in 2.0 mL of dimethyl acetamide/water/ethanol; 7:3:2) in a microwave vial. The reaction was heated to 150° C. for 150 seconds. After cooling, the mixture was filtered and loaded onto a reversed-phase preparative HPLC for purification. After freezing dry of pooled fractions, 71 mg (67%) of the product was obtained as a white powder.

Aufarbeitung

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. customloaded onto a reversed-phase preparative HPLC for purification
  4. customAfter freezing dry of pooled fractions

Quellen und Nachweise

ORD-Eintrag
ord-9c46ec21071849de95361dffa70df27a
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419979B2

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