4-Methylmorpholine → 6-(4-Isopropyl-piperazine-1-carbonyl)-nicotinic acid methyl ester

HRID 30454

Reaktionsgleichung

Reaktionsgleichung von HRID 30454
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])=O)=[N:9][CH:10]=1)=[O:4].Cl.Cl.[CH:16]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)([CH3:18])[CH3:17].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.CN1CCOCC1>C(Cl)Cl>[NH3:9].[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:6]=[CH:7][C:8]([C:11]([N:22]2[CH2:23][CH2:24][N:19]([CH:16]([CH3:18])[CH3:17])[CH2:20][CH2:21]2)=[O:13])=[N:9][CH:10]=1

Komponenten

8

Edukt 5

HCID 79724-MethylmorpholineHCID 3149925-(Methoxycarbonyl)pyridine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 122683781-Isopropylpiperazine dihydrochloride

Produkt 2

HCID 222AmmoniaAusbeute 2 %HCID 445157746-(4-Isopropyl-piperazine-1-carbonyl)-nicotinic acid methyl esterAusbeute 149,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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-8aa1265294d8459289e245119d19f9d8
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423147B2

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