Sodium Bicarbonate → 2-chloro-3-(1-cyano-1-methylethoxy)-N-[5-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}amino)-2-fluorophenyl]benzamide

HRID 1800649Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1800649
[Cl:1][C:2]1[C:10]([O:11][C:12]([C:15]#[N:16])([CH3:14])[CH3:13])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH2:17][C:18]1[CH:19]=[C:20]([NH:25][C:26]2[N:31]=[C:30]3[S:32][C:33]([NH:35][C:36]([CH:38]4[CH2:40][CH2:39]4)=[O:37])=[N:34][C:29]3=[CH:28][CH:27]=2)[CH:21]=[CH:22][C:23]=1[F:24].C(=O)([O-])O.[Na+]>CN(C)C(=O)C>[Cl:1][C:2]1[C:10]([O:11][C:12]([C:15]#[N:16])([CH3:14])[CH3:13])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:17][C:18]1[CH:19]=[C:20]([NH:25][C:26]2[N:31]=[C:30]3[S:32][C:33]([NH:35][C:36]([CH:38]4[CH2:40][CH2:39]4)=[O:37])=[N:34][C:29]3=[CH:28][CH:27]=2)[CH:21]=[CH:22][C:23]=1[F:24])=[O:5]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 86646062N-{5-[(3-amino-4-fluorophenyl)amino][1,3]thiazolo[5,4-b]pyridin-2-yl)cyclopropanecarboxamideHCID 866460652-Chloro-3-(1-cyano-1-methylethoxy)benzoyl chloride

Produkt 1

HCID 252063492-chloro-3-(1-cyano-1-methylethoxy)-N-[5-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}amino)-2-fluorophenyl]benzamideAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-3-(1-cyano-1-methylethoxy)benzoyl chloride synthesized above in N,N-dimethylacetamide (4.0 mL) was added N-{5-[(3-amino-4-fluorophenyl)amino][1,3]thiazolo[5,4-b]pyridin-2-yl)cyclopropanecarboxamide (200 mg, 0.582 mmol), and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution (20 mL), and the mixture was extracted with ethyl acetate (50 mL). The organic layer was washed with water (20 mL) and saturated brine (20 mL), and dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→0/100) and crystallized from hexane/ethyl acetate to give the title compound (216 mg, 66%) as pale-purple crystals.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate (50 mL)
  2. washThe organic layer was washed with water (20 mL) and saturated brine (20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→0/100)
  6. customcrystallized from hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-bb5c7da81829443baf0b5181ed221a3f
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344135B2

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