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Cesium carbonate → 2-(2-Chloro-6-fluorophenyl)-N-(2-methyl-6-morpholinopyrimidin-4-yl)thiazolo[5,4-c]pyridin-4-amine

HRID 2366199
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Reaktionsgleichung von HRID 2366199
Br[C:2]1[C:7]2[S:8][C:9]([C:11]3[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])=[N:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[CH3:19][C:20]1[N:25]=[C:24]([NH2:26])[CH:23]=[C:22]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[N:21]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([F:17])[C:11]=1[C:9]1[S:8][C:7]2[C:2]([NH:26][C:24]3[CH:23]=[C:22]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[N:21]=[C:20]([CH3:19])[N:25]=3)=[N:3][CH:4]=[CH:5][C:6]=2[N:10]=1
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Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 328000292-Methyl-6-morpholinopyrimidin-4-amineHCID 866689904-Bromo-2-(2-chloro-6-fluorophenyl)thiazolo[5,4-c]pyridine

Produkt 1

HCID 569532982-(2-Chloro-6-fluorophenyl)-N-(2-methyl-6-morpholinopyrimidin-4-yl)thiazolo[5,4-c]pyridin-4-amine
Ausbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a microwave tube was added 4-bromo-2-(2-chloro-6-fluorophenyl)thiazolo[5,4-c]pyridine (0.050 g, 1.5 mmol), 2-methyl-6-morpholinopyrimidin-4-amine (0.043 g, 0.22 mmol), Pd2(dba)3 (0.013 g, 0.017 mmol), XantPhos (0.017 g, 0.034 mmol) and Cs2CO3 (0.11 g, 0.34 mmol) in dioxane (2.0 mL). The mixture was degassed with N2 for 10 minutes and then irradiated in a microwave reactor at 160° C. for 2 hours. After cooling to room temperature, the solid was removed via filtration and the filtrate was concentrated under reduced pressure. The residue was purified with reverse phase column chromatography, eluting with a 0-60% gradient of CH3CN in 0.5% NH4HCO3 to give the desired product as a yellow solid (0.016 g, 24% yield). 1H NMR (500 MHz, DMSO-d6): δ 10.22 (s, 1H), 8.38 (d, J=5.5 Hz, 1H), 7.75 (d, J=5.5 Hz, 1H), 7.73-7.68 (m, 1H), 7.62-7.60 (m, 1H), 7.54-7.50 (m, 1H), 6.75 (s, 1H), 3.69-3.67 (m, 4H), 3.52-3.50 (m, 4H), 2.33 (s, 3H). LCMS (Method A): RT=6.16 min, m/z: 457.1 [M+H+].

Aufarbeitung

  1. customThe mixture was degassed with N2 for 10 minutes
  2. customirradiated in a microwave reactor at 160° C. for 2 hours
  3. customthe solid was removed via filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified with reverse phase column chromatography
  6. washeluting with a 0-60% gradient of CH3CN in 0.5% NH4HCO3

Quellen und Nachweise

ORD-Eintrag
ord-217b0ddde4234a638d737bd29ac6238c
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08697708B2

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