HCID 66669752, Verbindung → HCID 57710314, Verbindung

HRID 1038729Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1038729
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[N:13]=[C:14]=[O:15].[CH2:16]([N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][C:27]([NH:30][C:31]3[CH:36]=[C:35]([NH2:37])[N:34]=[CH:33][N:32]=3)=[CH:26][CH:25]=2)[CH2:20][CH2:19]1)[CH3:17]>CN1C(=O)CCC1>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[NH:13][C:14]([NH:37][C:35]1[CH:36]=[C:31]([NH:30][C:27]2[CH:28]=[CH:29][C:24]([N:21]3[CH2:22][CH2:23][N:18]([CH2:16][CH3:17])[CH2:19][CH2:20]3)=[CH:25][CH:26]=2)[N:32]=[CH:33][N:34]=1)=[O:15]

Komponenten

4

Edukt 2

HCID 66669752HCID 66669752, VerbindungHCID 860869932,6-Dichloro-3,5-dimethoxyphenyl isocyanate

Produkt 1

HCID 57710314HCID 57710314, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

2,6-dichloro-3,5-dimethoxyphenylisocyanate (1.2 eq.) is added to a solution of N-[4-(4-ethyl-piperazin-1-yl)-phenyl]-pyrimidine-4,6-diamine (350 mg, 1.18 mmol) in NMP (2 ml), at 70° C. and under an argon atmosphere. The resulting mixture is stirred at 70° C. for 2 h, allowed to cool to RT and concentrated. The residue is diluted with DCM and a saturated aqueous solution of sodium bicarbonate. The aqueous layer is separated and extracted with DCM. The organic phase is washed with brine, dried (sodium sulfate), filtered and concentrated. Purification of the crude product by trituration in MeOH followed by silica gel column chromatography (DCM/MeOH+1% NH3aq, 97:3) affords the title compound as a white solid:

Aufarbeitung

  1. temperatureto cool to RT
  2. concentrationconcentrated
  3. additionThe residue is diluted with DCM
  4. customThe aqueous layer is separated
  5. extractionextracted with DCM
  6. washThe organic phase is washed with brine
  7. dry with materialdried (sodium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification of the crude product by trituration in MeOH

Quellen und Nachweise

ORD-Eintrag
ord-87dcb4c970bc4d7da086923456dfaf1b
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552002B2

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