Tetrahydrofuran → N-cyclohexylmethyl-3-fluoro-5-methoxy-4-(2-propynyloxy)benzamide

HRID 601995Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 601995
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:15][CH3:16])[C:10]=1[O:11][CH2:12][C:13]#[CH:14])[C:5](Cl)=[O:6].O1CCCC1.[CH:22]1([CH2:28][NH2:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>C(N(CC)CC)C>[CH:22]1([CH2:28][NH:29][C:5](=[O:6])[C:4]2[CH:8]=[C:9]([O:15][CH3:16])[C:10]([O:11][CH2:12][C:13]#[CH:14])=[C:2]([F:1])[CH:3]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Komponenten

5

Edukt 3

HCID 8028Tetrahydrofuran2×HCID 76688CyclohexanemethylamineHCID 574456983-Fluoro-5-methoxy-4-(2-propynyloxy)benzoyl chloride

Produkt 1

HCID 57701145N-cyclohexylmethyl-3-fluoro-5-methoxy-4-(2-propynyloxy)benzamideAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 200 mg of 3-fluoro-5-methoxy-4-(2-propynyloxy)benzoyl chloride and 1 ml of tetrahydrofuran was added dropwise under ice cooling to a mixture of 5 ml of tetrahydrofuran, 93 mg of cyclohexylmethylamine and 100 mg of triethylamine. Then, the mixture obtained was stirred at room temperature for 0.5 hour. The reaction mixture was filtered. The filtrate was concentrated under reduced pressure. Water was added to the residue and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 223 mg of N-cyclohexylmethyl-3-fluoro-5-methoxy-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 45 of the present invention) represented by the formula:

Aufarbeitung

  1. customThen, the mixture obtained
  2. filtrationThe reaction mixture was filtered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with chloroform
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-395be85a29694ac7ba1802e257f66901
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902400B2

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