Dimethylformamide → 1-(2-Aminopyrimidin-4-yl)-6-iodoindazole-3-carbonyl chloride

HRID 1398584

Reaktionsgleichung

Reaktionsgleichung von HRID 1398584
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([I:17])[CH:15]=3)[C:10]([C:18]([OH:20])=O)=[N:9]2)[CH:5]=[CH:4][N:3]=1.S(Cl)([Cl:23])=O.CN(C=O)C>C(Cl)Cl>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([I:17])[CH:15]=3)[C:10]([C:18]([Cl:23])=[O:20])=[N:9]2)[CH:5]=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 681816001-(2-Aminopyrimidin-4-yl)-6-iodoindazole-3-carboxylic acid

Produkt 1

HCID 866695951-(2-Aminopyrimidin-4-yl)-6-iodoindazole-3-carbonyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 1-(2-aminopyrimidin-4-yl)-6-iodoindazole-3-carboxylic acid (1.00 g, 2.62 mmol) in DCM (10 mL), was added thionyl chloride (1.9 ml, 26.24 mmol)) followed by a drop of DMF. The mixture was stirred at 50° C. for 45 minutes. The reaction mixture was concentrated in vacuo and DCM (5 mL) was added and the concentration repeated (×2). The crude acid chloride was used directly in the next step: LC-MS m/z=+395.95 (M+H)+(after conversion to methyl ester derivative)

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo and DCM (5 mL)
  2. additionwas added
  3. concentrationthe concentration

Quellen und Nachweise

ORD-Eintrag
ord-4df54f96d4a845539760b1fd7505ef47
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901313B2

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