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Potassium Carbonate → N-(3-ethynyl-4-fluorophenyl)-7-methoxy-6-(3-(tetrahydro-2H-[1,4]dioxino[2,3-c]pyrrol-6(3H)-yl) propoxy)quinazolin-4-amine

HRID 712411
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 712411
[O:1]1[CH:6]2[CH2:7][NH:8][CH2:9][CH:5]2[O:4][CH2:3][CH2:2]1.[C:10]([C:12]1[CH:13]=[C:14]([NH:19][C:20]2[C:29]3[C:24](=[CH:25][C:26]([O:35][CH3:36])=[C:27]([O:30][CH2:31][CH2:32][CH2:33]Cl)[CH:28]=3)[N:23]=[CH:22][N:21]=2)[CH:15]=[CH:16][C:17]=1[F:18])#[CH:11].C([O-])([O-])=O.[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[C:10]([C:12]1[CH:13]=[C:14]([NH:19][C:20]2[C:29]3[C:24](=[CH:25][C:26]([O:35][CH3:36])=[C:27]([O:30][CH2:31][CH2:32][CH2:33][N:8]4[CH2:7][CH:6]5[O:1][CH2:2][CH2:3][O:4][CH:5]5[CH2:9]4)[CH:28]=3)[N:23]=[CH:22][N:21]=2)[CH:15]=[CH:16][C:17]=1[F:18])#[CH:11]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 82418726hexahydro-2H-[1,4]dioxino[2,3-c]pyrroleHCID 86729471N-(3-ethynyl-4-fluorophenyl)-6-(3-chloropropoxy)-7-methoxyquinazolin-4-amine

Produkt 1

HCID 86729472N-(3-ethynyl-4-fluorophenyl)-7-methoxy-6-(3-(tetrahydro-2H-[1,4]dioxino[2,3-c]pyrrol-6(3H)-yl) propoxy)quinazolin-4-amineAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553
Tetrabutylammonium Iodide
Katalysator
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of hexahydro-2H-[1,4]dioxino[2,3-c]pyrrole (0.40 g, 3.01 mmol, 1.0 eq), N-(3-ethynyl-4-fluorophenyl)-6-(3-chloropropoxy)-7-methoxyquinazolin-4-amine (0.87 g, 2.25 mmol, 0.75 eq), anhydrous K2CO3 (1.24 g, 9.0 mmol, 3.0 eq) and tetrabutylammonium iodide (55 mg, 0.15 mmol, 0.05 eq) in DMF (10 mL) was heated at 70° C. for 11 h. The reaction mixture was cooled to room temperature and quenched with water (10 mL). The resulted mixture was diluted with EtOAc (20 mL) and the organic phase was separated from the mixture. The water phase was extracted with EtOAc (20 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by a silica gel column chromatography (20:1 (v/v) CH2Cl2/CH3OH) to give the crude product, which was recrystallized from CH2Cl2/PE to afford the title compound as a pale yellow solid (0.47 g, 44.00%), HPLC: 96.10%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 480.1 (M+1); 1H NMR (400 MHz, CDCl3) δ: 2.05 (2H, m), 2.68 (2H, m), 2.72 (2H, m), 2.95 (2H, dd, J=3.6, 10.0 Hz), 3.06 (1H, br s), 3.56 (2H, m), 3.76 (2H, m), 3.95 (3H, s), 4.08 (2H, m), 4.15 (2H, t, J=8.4 Hz), 7.20 (1H, t, J=8.8 Hz), 8.07-8.15 (2H, m), 8.43 (1H, s), 8.64 (1H, s) ppm.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched with water (10 mL)
  3. additionThe resulted mixture was diluted with EtOAc (20 mL)
  4. customthe organic phase was separated from the mixture
  5. extractionThe water phase was extracted with EtOAc (20 mL×3)
  6. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. customthe residue was purified by a silica gel column chromatography (20:1 (v/v) CH2Cl2/CH3OH)
  10. customto give the crude product, which
  11. customwas recrystallized from CH2Cl2/PE

Quellen und Nachweise

ORD-Eintrag
ord-139054bd68e64eba82ffc4f31a126fdc
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09181277B2

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