Formic Acid → 4-[4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-2,6-dimethylpiperazine-1-carbaldehyde

HRID 2105989Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2105989
[CH3:1][CH:2]1[NH:7][CH:6]([CH3:8])[CH2:5][N:4]([CH2:9][C:10]([OH:28])([CH2:15][C:16]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[O:26][CH3:27])([CH3:18])[CH3:17])[C:11]([F:14])([F:13])[F:12])[CH2:3]1.[CH:29](OC=O)=[O:30].C(N=C=NC(C)C)(C)C.C(O)=O>C(Cl)Cl.N1C=CC=CC=1>[F:25][C:23]1[CH:22]=[CH:21][C:20]([O:26][CH3:27])=[C:19]([C:16]([CH3:18])([CH3:17])[CH2:15][C:10]([OH:28])([C:11]([F:12])([F:13])[F:14])[CH2:9][N:4]2[CH2:3][CH:2]([CH3:1])[N:7]([CH:29]=[O:30])[CH:6]([CH3:8])[CH2:5]2)[CH:24]=1

Komponenten

7

Edukt 4

HCID 284Formic AcidHCID 12734DiisopropylcarbodiimideHCID 9548680Formic anhydride2×HCID 57809802HCID 57809802, Verbindung

Produkt 1

HCID 103428654-[4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-2,6-dimethylpiperazine-1-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 2-(3,5-dimethylpiperazin-1-ylmethyl)-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol (20 mg) in methylene chloride (1 mL) at 0° C. was added pyridine (60.7 μL) followed by formic anhydride (2M in methylene chloride, 0.5 mL). (Formic anhydride was freshly prepared by slow addition of one equivalent of 1,3-diisopropylcarbodiimide to 2 equivalents of formic acid in methylene chloride. The resulting suspension was stirred for 1 hour, and filtered). The resulting mixture was stirred overnight for 20 hours, filtered through a cotton plug, poured into half-saturated aqueous sodium bicarbonate solution, and extracted twice with methylene chloride. The combined organic phases were dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by chromatography on silica gel (eluted with 5% methanol-methylene chloride) to give the title compound as a clear oil (19.3 mg).

Aufarbeitung

  1. filtrationfiltered)
  2. stirringThe resulting mixture was stirred overnight for 20 hours
  3. filtrationfiltered through a cotton plug
  4. additionpoured into half-saturated aqueous sodium bicarbonate solution
  5. extractionextracted twice with methylene chloride
  6. dry with materialThe combined organic phases were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography on silica gel (eluted with 5% methanol-methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-370790d94eb9424484f8c5e28901e465
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07579469B2

Notizen zur Reaktion

Wird geladen…