Dimethylformamide → N-(3-{[2-(acetylamino)-7-cyano-1,3-benzothiazol-6-yl]oxy}phenyl)-4-chloro-3-(1-cyano-1-methylethyl)benzamide

HRID 1097468

Reaktionsgleichung

Reaktionsgleichung von HRID 1097468
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[C:11]([C:14]#[N:15])([CH3:13])[CH3:12].C(Cl)(=O)C(Cl)=O.CN(C)C=O.[NH2:27][C:28]1[CH:29]=[C:30]([CH:47]=[CH:48][CH:49]=1)[O:31][C:32]1[CH:44]=[CH:43][C:35]2[N:36]=[C:37]([NH:39][C:40](=[O:42])[CH3:41])[S:38][C:34]=2[C:33]=1[C:45]#[N:46]>O1CCCC1.C(OCC)(=O)C>[C:40]([NH:39][C:37]1[S:38][C:34]2[C:33]([C:45]#[N:46])=[C:32]([O:31][C:30]3[CH:29]=[C:28]([NH:27][C:6](=[O:8])[C:5]4[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]([C:11]([C:14]#[N:15])([CH3:13])[CH3:12])[CH:4]=4)[CH:49]=[CH:48][CH:47]=3)[CH:44]=[CH:43][C:35]=2[N:36]=1)(=[O:42])[CH3:41]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 668104254-Chloro-3-(1-cyano-1-methylethyl)benzoic acidHCID 86644686N-[6-(3-aminophenoxy)-7-cyano-1,3-benzothiazol-2-yl]acetamide

Produkt 1

HCID 59454491N-(3-{[2-(acetylamino)-7-cyano-1,3-benzothiazol-6-yl]oxy}phenyl)-4-chloro-3-(1-cyano-1-methylethyl)benzamideAusbeute 66,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-chloro-3-(1-cyano-1-methylethyl)benzoic acid (83 mg, 0.370 mmol) in tetrahydrofuran (2 mL) were added oxalyl chloride (40 μL, 0.462 mmol) and N,N-dimethylformamide (5 μL), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in N,N-dimethylacetamide (2 mL). N-[6-(3-Aminophenoxy)-7-cyano-1,3-benzothiazol-2-yl]acetamide (100 mg, 0.308 mmol) produced in Example 12(ii) was added to the solution, and the mixture was stirred at room temperature for 10 hr. The reaction mixture was diluted with ethyl acetate (10 mL), washed successively with 5% aqueous sodium hydrogen carbonate solution (5 mL) and saturated brine (5 mL), and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was crystallized from ethyl acetate to give the title compound (108 mg, 66%) as a white powder.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in N,N-dimethylacetamide (2 mL)
  3. stirringthe mixture was stirred at room temperature for 10 hr
  4. washwashed successively with 5% aqueous sodium hydrogen carbonate solution (5 mL) and saturated brine (5 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationInsoluble material was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was crystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4025fc9cd9ba4c268406dc0fb7014dbd
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143258B2

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