Triethylamine → 3-{[3-(2-Chloro-6-fluoro-phenyl)-5-methyl-isoxazole-4-carbonyl]-amino}-piperidine-1-carboxylic acid methyl ester

HRID 2212181

Reaktionsgleichung

Reaktionsgleichung von HRID 2212181
C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:10]=1[C:16]1[C:20]([C:21](Cl)=[O:22])=[C:19]([CH3:24])[O:18][N:17]=1.[CH3:25][O:26][C:27]([N:29]1[CH2:34][CH2:33][CH2:32][CH:31]([NH2:35])[CH2:30]1)=[O:28]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:25][O:26][C:27]([N:29]1[CH2:34][CH2:33][CH2:32][CH:31]([NH:35][C:21]([C:20]2[C:16]([C:10]3[C:11]([F:15])=[CH:12][CH:13]=[CH:14][C:9]=3[Cl:8])=[N:17][O:18][C:19]=2[CH3:24])=[O:22])[CH2:30]1)=[O:28]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 27365813-(2-Chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonyl chlorideHCID 222730981-Piperidinecarboxylicacid,3-amino-,methylester(9CI)

Produkt 1

HCID 696523893-{[3-(2-Chloro-6-fluoro-phenyl)-5-methyl-isoxazole-4-carbonyl]-amino}-piperidine-1-carboxylic acid methyl esterAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Add 4-dimethylamino-pyridine (0.19 g, 1.5 mmol), triethylamine (3.2 mL, 23.2 mmol), and 3-(2-chloro-6-fluoro-phenyl)-5-methyl-isoxazole-4-carbonyl chloride (5.53 g, 20.1 mmol) to a solution of 3-amino-piperidine-1-carboxylic acid methyl ester (2.45 g, 15.5 mmol) in dichloromethane (100 mL). Stir the reaction at room temperature under nitrogen overnight. Wash the reaction with 1N HCl, saturated aqueous sodium bicarbonate solution, and brine; dry over magnesium sulfate; and concentrate. Purify by flash chromatography on silica gel (eluting with 0.75% methanol/chloroform) to give 5.49 g of the title compound as a yellow foam, 90% yield. 1H NMR: consistent with structure. MS (ion spray) 396 (M+).

Aufarbeitung

  1. customthe reaction at room temperature under nitrogen overnight
  2. washWash
  3. customthe reaction with 1N HCl, saturated aqueous sodium bicarbonate solution, and brine
  4. dry with materialdry over magnesium sulfate
  5. concentrationand concentrate
  6. customPurify by flash chromatography on silica gel (eluting with 0.75% methanol/chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-4dc73491067f45c29621accb2f726714
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07101891B2

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