Oxalyl chloride → N3-(5-Chlorothiophen-2-ylcarbonyl)-N2-[1-(4-pyridyl)piperidin-4-ylmethyl]-2,3-pyridinediamine

HRID 49843

Reaktionsgleichung

Reaktionsgleichung von HRID 49843
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[N:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][CH:25]([CH2:28][NH:29][C:30]3[C:35]([NH2:36])=[CH:34][CH:33]=[CH:32][N:31]=3)[CH2:24][CH2:23]2)=[CH:18][CH:17]=1>C(Cl)Cl.CN(C=O)C.N1C=CC=CC=1.C(Cl)(Cl)Cl>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:36][C:35]2[C:30]([NH:29][CH2:28][CH:25]3[CH2:26][CH2:27][N:22]([C:19]4[CH:18]=[CH:17][N:16]=[CH:21][CH:20]=4)[CH2:23][CH2:24]3)=[N:31][CH:32]=[CH:33][CH:34]=2)=[O:9])=[CH:4][CH:3]=1

Komponenten

8

Edukt 3

HCID 65578Oxalyl chlorideHCID 950485-Chloro-2-thiophenecarboxylic acidHCID 12150690N2-[1-(4-pyridyl)piperidin-4-ylmethyl]-2,3-pyridinediamine

Produkt 1

HCID 12990572N3-(5-Chlorothiophen-2-ylcarbonyl)-N2-[1-(4-pyridyl)piperidin-4-ylmethyl]-2,3-pyridinediamineAusbeute 62,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 1049PyridineLösungsmittelHCID 6212ChloroformLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 5-chlorothiophene-2-carboxylic acid (120 mg, 0.72 mmol) in methylene chloride and DMF (0.005 mL) was treated with oxalyl chloride (0.105 mL, 1.20 mmol). After 0.25 h, the mixture was concentrated and the residue was dissolved in chloroform. This solution was added dropwise to a solution of N2-[1-(4-pyridyl)piperidin-4-ylmethyl]-2,3-pyridinediamine (170 mg, 0.6 mmol) in pyridine and chloroform. The reaction mixture was then purified using a procedure similar to that described in Example 2, Part D, yielding 160 mg (58%) of the title compound as a hydrochloride salt.

Aufarbeitung

  1. concentrationthe mixture was concentrated
  2. dissolutionthe residue was dissolved in chloroform
  3. customThe reaction mixture was then purified

Quellen und Nachweise

ORD-Eintrag
ord-0208a0524ee5473484eeef0ced84e59f
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710057B2

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