Water → N-(3-{[2-(acetylamino)-1,3-benzothiazol-6-yl]oxy}phenyl)-3-(1-cyanocyclopropyl)benzamide

HRID 2190449Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2190449
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:13]=[C:14]([NH:18][C:19](=[O:31])[C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]5([C:29]#[N:30])[CH2:28][CH2:27]5)[CH:21]=4)[CH:15]=[CH:16][CH:17]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1.[C:32](Cl)(=[O:34])[CH3:33].C(N(CC)CC)C.O>O1CCCC1.C(OCC)(=O)C>[C:32]([NH:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:13]=[C:14]([NH:18][C:19](=[O:31])[C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]5([C:29]#[N:30])[CH2:27][CH2:28]5)[CH:21]=4)[CH:15]=[CH:16][CH:17]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1)(=[O:34])[CH3:33]

Komponenten

7

Edukt 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86655364N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]phenyl}-3-(1-cyanocyclopropyl)benzamide

Produkt 1

HCID 86655391N-(3-{[2-(acetylamino)-1,3-benzothiazol-6-yl]oxy}phenyl)-3-(1-cyanocyclopropyl)benzamideAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]phenyl}-3-(1-cyanocyclopropyl)benzamide (200 mg, 0.47 mmol) produced in Example A15(iii) in tetrahydrofuran (20 mL) were added acetyl chloride (0.3 mL, 4.22 mmol) and triethylamine (1.0 mL, 7.18 mmol), and the mixture was stirred at room temperature for 10 min. To the reaction mixture were added water (200 mL) and ethyl acetate (200 mL) and the mixture was stirred for 30 min. The organic layer was separated, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=20/80→0/100), and triturated with ethyl acetate/hexane to give the title compound (151 mg, 69%) as a colorless solid.

Aufarbeitung

  1. stirringthe mixture was stirred for 30 min
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=20/80→0/100)
  7. customtriturated with ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-99f6857670d84797a5a7d91eabf5ebeb
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324395B2

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