Triethylamine → Methyl 1-(5-{[methoxy(oxo)acetyl]amino}pyridin-2-yl)-4-methylpiperidine-4-carboxylate

HRID 1713904Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1713904
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][C:11]([CH3:18])([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.C(N(CC)CC)C.Cl[C:27](=[O:32])[C:28]([O:30][CH3:31])=[O:29]>C(Cl)Cl>[CH3:31][O:30][C:28](=[O:29])[C:27]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][C:11]([CH3:18])([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1)=[O:32]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 79846Methyl chloroglyoxylateHCID 59464146Methyl 1-(5-aminopyridin-2-yl)-4-methylpiperidine-4-carboxylate

Produkt 1

HCID 59464082Methyl 1-(5-{[methoxy(oxo)acetyl]amino}pyridin-2-yl)-4-methylpiperidine-4-carboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of methyl 1-(5-aminopyridin-2-yl)-4-methylpiperidine-4-carboxylate (2.96 g, 11.89 mmol) in DCM (100 mL) was added triethylamine (2.2 mL, 15.84 mmol) followed by methyl chlorooxoacetate (1.6 mL, 17.15 mmol) and the reaction mixture was allowed to stir at ambient temperature for 1.5 hrs. The reaction mixture was washed with brine (2×100 mL), the aqueous layer was re extracted with DCM (50 mL) and the organic washings were combined, dried and concentrated to leave the title compound as a brown gum (3.98 g, 11.89 mmol, 100%). 1H NMR (CDCl3) δ 1.72-1.82 (m, 2H), 1.96-2.02 (m, 2H), 2.52-2.59 (m, 1H), 2.95-3.03 (m, 2H), 3.70 (s, 3H), 3.97 (s, 3H), 4.16-4.22 (m, 2H), 6.67 (d, 1H), 7.93 (d, 1H), 8.28 (s, 1H), 8.66 (s, 1H); MS m/e MH+ 336.

Aufarbeitung

  1. washThe reaction mixture was washed with brine (2×100 mL)
  2. extractionthe aqueous layer was re extracted with DCM (50 mL)
  3. customdried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-494f2ad5a3034f4d83271e16b5fb64b2
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795283B2

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