4-Methylmorpholine → 6-[(4-Chloro-pyridine-2-carbonyl)-amino]-pyridine-2-carboxylic acid methyl ester

HRID 1040236

Reaktionsgleichung

Reaktionsgleichung von HRID 1040236
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8](O)=[O:9])[CH:3]=1.[NH2:11][C:12]1[N:17]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[CH:15]=[CH:14][CH:13]=1.CN1CCOCC1>CN(C)C=O>[CH3:21][O:20][C:18]([C:16]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:11][C:8]([C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][N:5]=2)=[O:9])[N:17]=1)=[O:19]

Komponenten

5

Edukt 3

HCID 79724-MethylmorpholineHCID 2308904-Chloropyridine-2-carboxylic acidHCID 13809143Methyl 6-aminopyridine-2-carboxylate

Produkt 1

HCID 668487256-[(4-Chloro-pyridine-2-carbonyl)-amino]-pyridine-2-carboxylic acid methyl esterAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-chloro-pyridine-2-carboxylic acid (16.3 g, 103 mmol), methyl 6-aminopicolinate (3.0 g, 18.6 mmol), (2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethylumnium hexafluorophosphate (HATU, 41.1 g, 108 mmol), and N-methyl morpholine (12.5 mL, 108 mmol) in N,N-dimethylformamide was stirred at room temperature for 12 hours. The solvent was removed under reduced pressure, and the residue suspended in acetonitrile. The solid thus obtained was isolated by filtration, washed with water (80 mL), acetonitrile (80 mL) and diethyl ether (80 m L) and dried under reduced pressure to afford 6-[(4-chloro-pyridine-2-carbonyl)-amino]-pyridine-2-carboxylic acid methyl ester as a white powder (25.6, 93% yield).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customThe solid thus obtained
  3. customwas isolated by filtration
  4. washwashed with water (80 mL), acetonitrile (80 mL) and diethyl ether (80 m L)
  5. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a075b9633701445f98265ed137feda08
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552196B2

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