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Dimethylformamide → 5-bromo-N-[4-chloro-5-({7-cyano-2-[(cyclopropylcarbonyl)amino]-1,3-benzothiazol-6-yl}oxy)-2-fluorophenyl]-1-methyl-1H-pyrazole-4-carboxamide

HRID 455201
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 455201
[Br:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:8]([OH:10])=O.C(Cl)(=O)C(Cl)=O.CN(C)C=O.[NH2:22][C:23]1[C:24]([F:48])=[CH:25][C:26]([Cl:47])=[C:27]([CH:46]=1)[O:28][C:29]1[CH:43]=[CH:42][C:32]2[N:33]=[C:34]([NH:36][C:37]([CH:39]3[CH2:41][CH2:40]3)=[O:38])[S:35][C:31]=2[C:30]=1[C:44]#[N:45]>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:8]([NH:22][C:23]1[CH:46]=[C:27]([O:28][C:29]2[CH:43]=[CH:42][C:32]3[N:33]=[C:34]([NH:36][C:37]([CH:39]4[CH2:41][CH2:40]4)=[O:38])[S:35][C:31]=3[C:30]=2[C:44]#[N:45])[C:26]([Cl:47])=[CH:25][C:24]=1[F:48])=[O:10]
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Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 596795725-bromo-1-methyl-1H-pyrazole-4-carboxylic acidHCID 86644692N-[6-(5-amino-2-chloro-4-fluorophenoxy)-7-cyano-1,3-benzothiazol-2-yl]cyclopropanecarboxamide

Produkt 1

HCID 594545115-bromo-N-[4-chloro-5-({7-cyano-2-[(cyclopropylcarbonyl)amino]-1,3-benzothiazol-6-yl}oxy)-2-fluorophenyl]-1-methyl-1H-pyrazole-4-carboxamide
Ausbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 5-bromo-1-methyl-1H-pyrazole-4-carboxylic acid (68 mg, 0.331 mmol) in tetrahydrofuran (1 mL) were added oxalyl chloride (35 μL, 0.408 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 (1 mL). N-[6-(5-Amino-2-chloro-4-fluorophenoxy)-7-cyano-1,3-benzothiazol-2-yl]cyclopropanecarboxamide (90 mg, 0.223 mmol) produced in Example 23(vi) was added to the solution, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with ethyl acetate (15 mL), washed successively with 5% aqueous sodium hydrogen carbonate solution (7 mL) and saturated brine (7 mL), and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=60/40→100/0), and the obtained solution was concentrated under reduced pressure. The residue was crystallized from ethyl acetate to give the title compound (34 mg, 26%) as a white powder.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in N,N-dimethylacetamide (1 mL)
  3. stirringthe mixture was stirred at room temperature for 1 hr
  4. washwashed successively with 5% aqueous sodium hydrogen carbonate solution (7 mL) and saturated brine (7 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 purified by silica gel column chromatography (ethyl acetate/n-hexane=60/40→100/0)
  9. concentrationthe obtained solution was concentrated under reduced pressure
  10. customThe residue was crystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-300aa824581d4f81a398787f40aa5f1c
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08497274B2

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