Reaktion #162057

ord-1f3329bc03114cd9aae1109039c9033a

Reaktionsgleichung

CCCS(=O)(=O)Cl
1-propanesulfonyl chloride
Fc1cnc(-c2c[nH]c3ncc(Cl)cc23)nc1NC1CCCNC1
2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-N-(piperidin-3-yl)pyrimidin-4-amine
CCN(C(C)C)C(C)C
iPr2NEt
CCCS(=O)(=O)N1CCC[C@@H](Nc2nc(-c3c[nH]c4ncc(Cl)cc34)ncc2F)C1
desired product
CCCS(=O)(=O)N1CCC[C@@H](Nc2nc(-c3c[nH]c4ncc(Cl)cc34)ncc2F)C1
(R)-2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-N-(1-(propylsulfonyl)piperidin-3-yl)pyrimidin-4-amine

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe resulting residue was purified by preparatory HPLC (0.1% TFA-H2O/acetonitrile)

Vorschrift

To a solution of 2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-N-(piperidin-3-yl)pyrimidin-4-amine, 5c, (0.40 g, 1.15 mmol) in 10:1 mixture of CH2Cl2/DMF (8 mL) was added iPr2NEt (0.60 mL, 3.46 mmol) followed by 1-propanesulfonyl chloride (0.13 mL, 1.15 mmol). The reaction mixture was stirred at room temperature for 5 hours. The resulting residue was purified by preparatory HPLC (0.1% TFA-H2O/acetonitrile) to afford the desired product, 316.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08829007B2uspto-grants-2014_09