1,2-Dichloroethane → (4-Isopropyl-piperazin-1-yl)-[6-(2-piperidin-1-yl-ethylamino)-pyridin-3-yl]-methanone

HRID 551587

Reaktionsgleichung

Reaktionsgleichung von HRID 551587
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH:16]([CH3:18])[CH3:17])[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.Cl[C:20]1[CH:28]=[CH:27][C:23](C(O)=O)=[CH:22][N:21]=1.[CH:29]([N:32]1CCNCC1)(C)[CH3:30].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CN1CCOCC1>C(Cl)Cl.[OH-].[Na+]>[NH3:7].[CH:16]([N:13]1[CH2:14][CH2:15][N:10]([C:8]([C:5]2[CH:6]=[N:7][C:2]([NH:32][CH2:29][CH2:30][N:21]3[CH2:20][CH2:28][CH2:27][CH2:23][CH2:22]3)=[CH:3][CH:4]=2)=[O:9])[CH2:11][CH2:12]1)([CH3:18])[CH3:17]

Komponenten

10

Edukt 6

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 780131-IsopropylpiperazineHCID 792226-Chloronicotinic acidHCID 43420904(6-Chloro-pyridin-3-yl)-(4-isopropyl-piperazin-1-yl)-methanone

Produkt 2

HCID 222AmmoniaAusbeute 2 %HCID 11710212(4-Isopropyl-piperazin-1-yl)-[6-(2-piperidin-1-yl-ethylamino)-pyridin-3-yl]-methanoneAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

(6-Chloro-pyridin-3-yl)-(4-isopropyl-piperazin-1-yl)-methanone. To a solution of 6-chloronicotinic acid (0.985 g, 6.25 mmol) and 1-isopropyl-piperazine (1.50 g, 7.50 mmol) in DCM (100 mL) was added HOBt (1.20 g, 9.40 mmol), EDC (1.80 g, 9.40 mmol), and N-methyl morpholine (3.4 mL, 31.3 mmol). After 18 h the reaction was diluted with 1 N NaOH (50 mL) and extracted with DCM (3×50 mL). The organic extracts were combined, dried (Na2SO4), and concentrated. Chromatography of the residue (SiO2: 2-4% 2 M NH3 in MeOH/DCM) gave the title compound as a solid (0.934 g, 56%).

Aufarbeitung

  1. extractionextracted with DCM (3×50 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f19ecca019454a139282c3ef390b44e3
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947718B2

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