Acetic Acid → N-(5-chloropyridin-2-yl)-5-iodo-2-[(1-isopropylpiperidin-4-ylcarbonyl)amino]benzamide

HRID 988702Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 988702
F[C:2](F)(F)[C:3](O)=O.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:33])[C:17]2[CH:22]=[C:21]([I:23])[CH:20]=[CH:19][C:18]=2[NH:24][C:25]([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[O:26])=[N:13][CH:14]=1.[C:34](O)(=O)C.C([BH3-])#N.[Na+].C([O-])(=O)C.[NH4+]>CO.CC(C)=O>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:33])[C:17]2[CH:22]=[C:21]([I:23])[CH:20]=[CH:19][C:18]=2[NH:24][C:25]([CH:27]2[CH2:28][CH2:29][N:30]([CH:2]([CH3:3])[CH3:34])[CH2:31][CH2:32]2)=[O:26])=[N:13][CH:14]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 21906457N-(5-chloropyridin-2-yl)-5-iodo-2-[(4-piperidinylcarbonyl)amino]benzamide trifluoroacetate

Produkt 1

HCID 21906277N-(5-chloropyridin-2-yl)-5-iodo-2-[(1-isopropylpiperidin-4-ylcarbonyl)amino]benzamideAusbeute 65,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirring suspension of N-(5-chloropyridin-2-yl)-5-iodo-2-[(4-piperidinylcarbonyl)amino]benzamide trifluoroacetate (1.5 g, 2.52 mmol) in methanol (25 mL) was added acetone (25 mL), followed by acetic acid (0.6 mL, 10 mmol), and then sodium cyanoborohydride (0.67 g, 10 mmol). After stirring overnight, the solution was treated with saturated aqueous ammonium acetate solution, concentrated, and partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic phase was washed with brine, dried over magnesium sulfate, filtered, and concentrated. The crude product was purified by chromatography over silica gel, eluting with a step gradient of 5-15% 2 M solution of ammonia/methanol in dichloromethane. The chromatography product was slurried in diethyl ether and filtered to give 0.87 g (65%) of a white solid.

Aufarbeitung

  1. concentrationconcentrated
  2. custompartitioned between dichloromethane and saturated aqueous sodium bicarbonate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by chromatography over silica gel
  8. washeluting with a step gradient of 5-15% 2 M solution of ammonia/methanol in dichloromethane
  9. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-5da9af3ff4144dbb9ff4740ebe84f6f3
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06635657B1

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