Pyridine → HCID 86623464, Verbindung

HRID 639456Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 639456
[NH2:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:6]2[C:5]2[CH:16]=[CH:17][N:18]([CH2:19][CH2:20][OH:21])[C:4]=2[N:3]=1.N1C=CC=CC=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C1COCC1>[CH3:28][S:29]([O:21][CH2:20][CH2:19][N:18]1[C:4]2[N:3]=[C:2]([NH2:1])[N:7]3[N:8]=[C:9]([C:11]4[O:12][CH:13]=[CH:14][CH:15]=4)[N:10]=[C:6]3[C:5]=2[CH:16]=[CH:17]1)(=[O:31])=[O:30]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 684140642-{5-amino-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl}ethanol

Produkt 1

HCID 86623464HCID 86623464, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of the title C compound, 2-{5-amino-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl}ethanol (15 g, 5.28 mmol) in 45 mL of dry THF is added 75 mL of TEA, 75 mL of pyridine and methanesulfonyl chloride (0.6 mL, 7.75 mmol) at 0° C. The mixture is stirred at RT under N2 for 12 h. The solvent is evaporated in vacuo and the residue is purified by flash chromatography using EtOAc as eluent to give 2-{5-amino-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl}ethyl methanesulfonate as a white solid: LC/MS (M+1=363.4). 1H NMR (DMSO-d6, 400 MHz) δ 3.07 (s, 3H), 4.47 (t, 2H, J=5.2 Hz), 4=59 (t, 2H) J=5.2 Hz), 6.65 (d, 1H, J=3.6 Hz), 6.72 (dd, 1H, J=3.2 Hz and 1.6 Hz), 7.18 (d, 1H, J=3.6 Hz), 7.20 (d, 1H, J=3.2 Hz), 7.60 (s, 2H), 7.92 (d, 1H, J=1.2 Hz).

Aufarbeitung

  1. customThe solvent is evaporated in vacuo
  2. customthe residue is purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fcb8df95d2e04f6da18dfb86dbcd8187
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691869B2

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