Triacetoxyperiodinane → HCID 89922524, Verbindung

HRID 921848Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 921848
[Cl:1][C:2]1[C:7]([CH:8]([CH3:11])[CH2:9][OH:10])=[CH:6][C:5]([C:12]#[N:13])=[CH:4][C:3]=1[NH:14][C:15]1[N:20]=[C:19]([N:21]([CH:31]2[CH2:33][CH2:32]2)[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:18]2=[N:34][CH:35]=[C:36]([C:37]#[N:38])[N:17]2[N:16]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[C:7]([CH:8]([CH3:11])[CH:9]=[O:10])=[CH:6][C:5]([C:12]#[N:13])=[CH:4][C:3]=1[NH:14][C:15]1[N:20]=[C:19]([N:21]([CH:31]2[CH2:32][CH2:33]2)[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:18]2=[N:34][CH:35]=[C:36]([C:37]#[N:38])[N:17]2[N:16]=1

Komponenten

4

Edukt 2

HCID 159087Triacetoxyperiodinane2×HCID 89922862HCID 89922862, Verbindung

Produkt 1

HCID 89922524HCID 89922524, VerbindungAusbeute 67,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-((2-chloro-5-cyano-3-(1-hydroxypropan-2-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (37 mg, 0.070 mmol) was taken up in DCM (1 mL) and the solution was cooled to 0° C. Dess-Martin periodinane (35.6 mg, 0.084 mmol) was added, and the reaction was stirred at 0° C. for 1.5 h. Some SM still remaining, so an additional 0.4 eq. (12 mg) of Dess-Martin was added, and the reaction was stirred for 30 min. The reaction was quenched with 2M K3PO4 and extracted with DCM. The organic layer was dried over Na2SO4, filtered, and concentrated. The material was purified by flash column chromatography (0%-60% EtOAc/Hex; 12 g column). 2-((2-chloro-5-cyano-3-(1-oxopropan-2-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (25 mg) was obtained as a glassy liquid.

Aufarbeitung

  1. stirringthe reaction was stirred for 30 min
  2. customThe reaction was quenched with 2M K3PO4
  3. extractionextracted with DCM
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe material was purified by flash column chromatography (0%-60% EtOAc/Hex; 12 g column)

Quellen und Nachweise

ORD-Eintrag
ord-ad29713f89d8402ca0dacc569958619d
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273057B2

Notizen zur Reaktion

Wird geladen…