2-[(1R)-1-Chloroethyl]-3-fluoropyridine → HCID 25064543, Verbindung

HRID 1694547Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1694547
[NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:12][OH:13])=[N:8][C:7]([SH:18])=[N:6][C:5]=2[N:19]=1.Cl[C@@H:21]([C:23]1[C:28]([F:29])=[CH:27][CH:26]=[CH:25][N:24]=1)[CH3:22]>>[NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH2:14][CH:15]([CH3:16])[CH3:17])[CH2:12][OH:13])=[N:8][C:7]([S:18][C@H:21]([C:23]3[C:28]([F:29])=[CH:27][CH:26]=[CH:25][N:24]=3)[CH3:22])=[N:6][C:5]=2[N:19]=1

Komponenten

3

Edukt 2

HCID 598688232-[(1R)-1-Chloroethyl]-3-fluoropyridineHCID 178445911HCID 178445911, Verbindung

Produkt 1

HCID 25064543HCID 25064543, VerbindungAusbeute 47 %

Versuchsvorschrift

The title compound was prepared using General method A starting from (2R)-2-[(2-amino-5-mercapto[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol (348 mg, 1.16 mmol) and 2-((R)-1-chloroethyl)-3-fluoro-pyridine (240 mg, 1.5 mmol). Purification by flash column chromatography (eluent DCM:methanol gradient) resulted in 190 mg (47% yield) of the title compound with a diastereomeric excess of 60%. Of this material 55 mg was further purified by preparative HPLC. The last eluting isomer was collected to yield 21 mg of the title compound.

Aufarbeitung

  1. customThe title compound was prepared
  2. customPurification by flash column chromatography (eluent DCM:methanol gradient)

Quellen und Nachweise

ORD-Eintrag
ord-dd564f6d6bd24c8692feb446c2775d99
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158785B2

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