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Sodium Carbonate → HCID 178480979, Verbindung

HRID 897912
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 897912
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[N:4]([CH:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)[N:3]=1.CC1(C)C(C)(C)OB([C:33]2[CH:38]=[CH:37][C:36]([NH:39][C:40]3[O:41][C:42]4[CH:48]=[CH:47][C:46]([O:49][C:50]([F:53])([F:52])[F:51])=[CH:45][C:43]=4[N:44]=3)=[CH:35][CH:34]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.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>[NH2:11][C:9]1[N:8]=[CH:7][N:6]=[C:5]2[N:4]([C@H:12]3[CH2:17][CH2:16][C@@H:15]([N:18]4[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]4)[CH2:14][CH2:13]3)[N:3]=[C:2]([C:33]3[CH:34]=[CH:35][C:36]([NH:39][C:40]4[O:41][C:42]5[CH:48]=[CH:47][C:46]([O:49][C:50]([F:51])([F:52])[F:53])=[CH:45][C:43]=5[N:44]=4)=[CH:37][CH:38]=3)[C:10]=12
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 208170473-iodo-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amineHCID 22346974N-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-(trifluoromethoxy)-2-benzoxazolamine2×

Produkt 1

HCID 178480979HCID 178480979, VerbindungAusbeute 78,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397
HCID 178418397, Verbindung
Katalysator
2×
HCID 962WaterLösungsmittel
HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 3-iodo-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.06 g, 0.00014 mol), N2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-(trifluoromethoxy)-1,3-benzoxazol-2-amine (0.071 g, 0.00017 mol), tetrakis(triphenylphosphine)palladium (0.011 g, 0.00001 mol) and sodium carbonate (0.037, 0.00035 mol) in ethylene glycol dimethyl ether (3 mL) and water (1 mL) was heated at 80° C. for 16 hours. Additional N2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-(trifluoromethoxy)-1,3-benzoxazol-2-amine (0.030 g, 0.00007 mol) and tetrakis(triphenylphosphine)palladium (0.005 g, 0.000004 mol) were added, and the mixture was stirred at 80° C. for 5 hours under atmosphere of nitrogen. The mixture was allowed to cool to ambient temperature, and the solvent was removed under the reduced pressure. The residue was partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with water, saturated aqueous sodium bicarbonate solution, and brine, and dried over magnesium sulfate. The solvents were evaporated under the reduced pressure, and the residue was purified by flash column chromatography on silica using 2% aqueous ammonium hydroxide solution/5%-25% methanol/dichloromethane as a mobile phase. The solvent was removed under reduced pressure to give cis-N2-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5-(trifluoromethoxy)-1,3-benzoxazol-2-amine (0.065 g, 0.00011 mol). 1H NMR (DMSO-d6, 400 MHz) δ 11.25 (s, 1H), 8.20 (s, 1H), 7.95 (d, 2H), 7.65 (m, 3H), 7.50 (s, 1H), 7.15 (s, 1H), 4.80 (br, 1H), 2.60 (br, 9H), 2.49 (s, 3H), 2.20 (br, 3H), 2.10 (br, 1H), 1.75 (br, 2H), 1.60 (br, 2H). RP-HPLC (Delta Pak C18, 5 μm, 300 A, 15 cm; 5%-95% acetonitrile-0.1M ammonium acetate over 10 min, 1 mL/min) Rt 10.7 min. MS: MH+608

Aufarbeitung

  1. temperatureto cool to ambient temperature
  2. customthe solvent was removed under the reduced pressure
  3. customThe residue was partitioned between water and ethyl acetate
  4. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
  5. washThe combined organic extracts were washed with water, saturated aqueous sodium bicarbonate solution, and brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvents were evaporated under the reduced pressure
  8. customthe residue was purified by flash column chromatography on silica using 2% aqueous ammonium hydroxide solution/5%-25% methanol/dichloromethane as a mobile phase
  9. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e046697fdf134e919728d040d5c3b5aa
Quelldatensatz
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06921763B2

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