Water → 4-(4-chloro-6-(5-isopropyl-2-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-3,5-dimethyl-1H-indazole-1-carbaldehyde

HRID 80851

Reaktionsgleichung

Reaktionsgleichung von HRID 80851
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH3:32])[C:9]=2[C:11]2[N:12]=[C:13](O)[C:14]3[CH2:20][N:19]([C:21]4[CH:26]=[C:25]([CH:27]([CH3:29])[CH3:28])[CH:24]=[CH:23][C:22]=4[CH3:30])[CH2:18][CH2:17][C:15]=3[N:16]=2)[NH:4][N:3]=1.[CH3:33][N+](C)=C[Cl:36].[Cl-:38].[OH2:39]>ClCCCl>[Cl:36][C:13]1[C:14]2[CH2:20][N:19]([C:21]3[CH:26]=[C:25]([CH:27]([CH3:29])[CH3:28])[CH:24]=[CH:23][C:22]=3[CH3:30])[CH2:18][CH2:17][C:15]=2[N:16]=[C:11]([C:9]2[C:8]([CH3:32])=[CH:7][CH:6]=[C:5]3[C:10]=2[C:2]([CH3:1])=[N:3][NH:4]3)[N:12]=1.[Cl:38][C:13]1[C:14]2[CH2:20][N:19]([C:21]3[CH:26]=[C:25]([CH:27]([CH3:28])[CH3:29])[CH:24]=[CH:23][C:22]=3[CH3:30])[CH2:18][CH2:17][C:15]=2[N:16]=[C:11]([C:9]2[C:8]([CH3:32])=[CH:7][CH:6]=[C:5]3[C:10]=2[C:2]([CH3:1])=[N:3][N:4]3[CH:33]=[O:39])[N:12]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 178424912HCID 178424912, Verbindung

Produkt 2

HCID 866902884-(4-chloro-6-(5-isopropyl-2-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-3,5-dimethyl-1H-indazole-1-carbaldehydeHCID 178424910HCID 178424910, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a suspension of 2-(3,5-dimethyl-1H-indazol-4-yl)-6-(5-isopropyl-2-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ol (1.3 g, 3.04 mmol) in DCE (50 mL) was added Vilsmeier reagent (1.95 g, 15.2 mmol). The mixture was heated at 50° C. for 2 h. LC-MS showed reaction complete. The reaction mixture was poured into water, and the layers were separated. The aqueous layer was extracted with DCM. The organics were combined and concentrated. The residue was purified by FCC (0-100% EtOAc/heptane) to provide 4-chloro-2-(3,5-dimethyl-1H-indazol-4-yl)-6-(5-isopropyl-2-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine MS (ESI+) m/z 446.3 (M+H)+ and 4-(4-chloro-6-(5-isopropyl-2-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-3,5-dimethyl-1H-indazole-1-carbaldehyde MS (ESE) m/z 474.3 (M+H)+.

Aufarbeitung

  1. customreaction complete
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with DCM
  4. concentrationconcentrated
  5. customThe residue was purified by FCC (0-100% EtOAc/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-cd341f6566c64530a0ac3e7817106fd5
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846656B2

Verknüpfte Notizen

Wird geladen…