Sodium Carbonate → 1-{4-(Methylamino)-6-[4-(methoxy)phenyl]-1,3,5-triazin-2-yl}-N-{[2-(trifluoromethyl)phenyl]methyl}-4-piperidinecarboxamide

HRID 1678434Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1678434
O1[CH2:6][CH2:5][O:4][CH2:3]C1.Cl[C:8]1[N:13]=[C:12]([NH:14][CH3:15])[N:11]=[C:10]([N:16]2[CH2:21][CH2:20][CH:19]([C:22]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:35])([F:34])[F:33])=[O:23])[CH2:18][CH2:17]2)[N:9]=1.[CH3:36][C:37]1C=CC=[CH:39][C:38]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.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.O.CC#N>[CH3:15][NH:14][C:12]1[N:13]=[C:8]([C:37]2[CH:36]=[CH:6][C:5]([O:4][CH3:3])=[CH:39][CH:38]=2)[N:9]=[C:10]([N:16]2[CH2:17][CH2:18][CH:19]([C:22]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:33])([F:35])[F:34])=[O:23])[CH2:20][CH2:21]2)[N:11]=1

Komponenten

9

Edukt 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27332672-Methylphenyl boronic acidHCID 866443121-[4-chloro-6-(methylamino)-1,3,5-triazin-2-yl]-N-{[-(trifluoromethyl)phenyl]methyl}-4-piperidinecarboxamide2×

Produkt 1

HCID 594477541-{4-(Methylamino)-6-[4-(methoxy)phenyl]-1,3,5-triazin-2-yl}-N-{[2-(trifluoromethyl)phenyl]methyl}-4-piperidinecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

In a microwave vial, to a 1,4-dioxane (3.0 ml) suspension of 1-[4-chloro-6-(methylamino)-1,3,5-triazin-2-yl]-N-{[2-(trifluoromethyl)phenyl]methyl}-4-piperidine carboxamide (Intermediate 7d, 75 mg, 0.17 mmol, 1.0 equiv) was added (2-methylphenyl)boronic acid (29 mg, 0.21 mmol, 1.2 equiv), Na2CO3 (37 mg, 0.35 mmol, 2.0 equiv) in 3:1 CH3CN:H2O, and lastly Pd(PPh3)4 (10 mg, 0.0088 mmol, 0.05 equiv). The reaction mixture was heated at 150° C. for 25 minutes. The resulting suspension was diluted with ethyl acetate (10 ml), washed with water (5 ml), dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was taken up in 2.0 ml DMSO and purified via reverse-phase HPLC purification to afford the title compound. MS (ES+): m/e 501.0 [M+H]+.

Aufarbeitung

  1. washwashed with water (5 ml)
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. custompurified via reverse-phase HPLC purification

Quellen und Nachweise

ORD-Eintrag
ord-aa55639da5b7455fa0b541556a26e5e9
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008483B2

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