4-Methylmorpholine → (4-Isopropyl-piperazin-1-yl)-(5-piperidin-1-ylmethyl-pyridin-2-yl)-methanone

HRID 551578

Reaktionsgleichung

Reaktionsgleichung von HRID 551578
CO[C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH:18]([CH3:20])[CH3:19])[CH2:14][CH2:13]2)=[O:11])=[N:6][CH:5]=1.COC([C:26]1[CH:27]=[CH:28][C:29](C(O)=O)=[N:30][CH:31]=1)=O.Cl.Cl.C(N1CCNCC1)(C)C.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.CN1CCOCC1>C(Cl)Cl>[NH3:6].[CH:18]([N:15]1[CH2:16][CH2:17][N:12]([C:10]([C:7]2[CH:8]=[CH:9][C:4]([CH2:3][N:30]3[CH2:31][CH2:26][CH2:27][CH2:28][CH2:29]3)=[CH:5][N:6]=2)=[O:11])[CH2:13][CH2:14]1)([CH3:20])[CH3:19]

Komponenten

9

Edukt 6

HCID 79724-MethylmorpholineHCID 3149925-(Methoxycarbonyl)pyridine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 122683781-Isopropylpiperazine dihydrochlorideHCID 445157746-(4-Isopropyl-piperazine-1-carbonyl)-nicotinic acid methyl ester

Produkt 2

HCID 222AmmoniaAusbeute 2 %HCID 25126154(4-Isopropyl-piperazin-1-yl)-(5-piperidin-1-ylmethyl-pyridin-2-yl)-methanoneAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

6-(4-Isopropyl-piperazine-1-carbonyl)-nicotinic acid methyl ester. To a solution of pyridine-2,5-dicarboxylic acid 5-methyl ester (1.00 g, 5.50 mmol) and 1-isopropyl-piperazine dihydrochloride (1.20 g, 6.10 mmol) in DCM (100 mL) was added 1-hydroxybenzotriazole hydrate (HOBt, 1.10 g, 8.30 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC, 1.60 g, 8.30 mmol), and N-methyl morpholine (2.9 mL, 27.0 mmol). After 18 h, the reaction mixture was quenched with 1 N aq. NaHCO3 (50 mL) and extracted with DCM (3×50 mL). The organic layers were combined, dried (Na2SO4), and concentrated. Chromatography of the residue (SiO2; 2-5% 2 M NH3 in MeOH/DCM) gave the title compound (1.20 g, 74%).

Aufarbeitung

  1. customthe reaction mixture was quenched with 1 N aq. NaHCO3 (50 mL)
  2. extractionextracted with DCM (3×50 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d3e3bf082b0746e98c813168336111a5
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947718B2

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