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Sodium Carbonate → HCID 59379868, Verbindung

HRID 2353712
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2353712
[CH:1]1([NH:4][C:5](=[O:16])[NH:6][C:7]2[CH:12]=[CH:11][C:10](B(O)O)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.Cl[C:18]1[N:23]=[C:22]([C:24]([S:27]([CH:30]2[CH2:32][CH2:31]2)(=[O:29])=[O:28])([CH3:26])[CH3:25])[CH:21]=[C:20]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][C@@H:34]2[CH3:39])[N:19]=1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC.O.CCO>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:1]1([NH:4][C:5](=[O:16])[NH:6][C:7]2[CH:12]=[CH:11][C:10]([C:18]3[N:23]=[C:22]([C:24]([S:27]([CH:30]4[CH2:31][CH2:32]4)(=[O:28])=[O:29])([CH3:26])[CH3:25])[CH:21]=[C:20]([N:33]4[CH2:38][CH2:37][O:36][CH2:35][C@@H:34]4[CH3:39])[N:19]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 57427756[4-(3-Cyclopropylureido)phenyl]boronic acidHCID 59380019HCID 59380019, VerbindungHCID 86587095Dimethoxyethane ethanol water

Produkt 1

HCID 59379868HCID 59379868, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476
HCID 178418476, Verbindung
Katalysator
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

[4-(3-Cyclopropylureido)phenyl]boronic acid, pinacol ester (199 mg, 0.66 mmol), 2-chloro-4-(2-cyclopropylsulfonylpropan-2-yl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine (190 mg, 0.53 mmol), sodium carbonate (1.320 mL, 2.64 mmol) and dichlorobis(triphenylphosphine)palladium(II) (37.1 mg, 0.05 mmol) were suspended in 18% DMF in a DME:Water:EtOH 7:3:2 solution (4 mL) and sealed into a microwave tube. The reaction was heated to 100° C. for 20 minutes in the microwave reactor and cooled to RT. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M ammonia in methanol and pure fractions were evaporated to dryness. The crude product was further purified by preparative HPLC using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents, to give the desired material as a white solid (85 mg).

Aufarbeitung

  1. customsealed into a microwave tube
  2. temperaturecooled to RT
  3. customThe crude product was purified by ion exchange chromatography
  4. washThe desired product was eluted from the column
  5. customwere evaporated to dryness
  6. customThe crude product was further purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-ab112ebc83604480a1cbd366c0e17bc8
Quelldatensatz
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07750003B2

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