Hydrochloric Acid → HCID 42605479, Verbindung

HRID 1712182Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1712182
C(O[C:6](=O)[NH:7][C:8]1[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:9]=1[NH2:16])(C)(C)C.[CH:18]1(C=O)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[Cl:26][C:27]1[CH:37]=[CH:36][CH:35]=[CH:34][C:28]=1[O:29][CH2:30][C:31](O)=O.[CH:38]1([N+:44]#[C-:45])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1.Cl.C[OH:48]>O1CCOCC1>[Cl:26][C:27]1[CH:37]=[CH:36][CH:35]=[CH:34][C:28]=1[O:29][CH2:30][C:31]1[N:7]([CH:6]([CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[C:45]([NH:44][CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)=[O:48])[C:8]2[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:9]=2[N:16]=1

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 887MethanolHCID 119692-Chlorophenoxyacetic acidHCID 16275CyclohexanecarboxaldehydeHCID 79129Cyclohexyl isocyanideHCID 66619231tert-Butyl (2-amino-4,5-difluorophenyl)carbamate2×

Produkt 1

HCID 42605479HCID 42605479, VerbindungAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of (2-amino-4,5-difluoro-phenyl)-carbamic acid tert-butyl ester (24.42 mg, 0.10 mmol, 1.0 equiv; Intermediate C) in MeOH (1.0 mL) was added cyclohexanecarbaldehyde (16.83 mg, 18.05 μl, 0.15 mmol, 1.5 equiv; [2043-61-0]) and the mixture stirred at rt. After 30 min, (2-chloro-phenoxy)-acetic acid (18.66 mg, 0.10 mmol, 1.0 equiv; [CAS RN 614-61-9]) and cyclohexyl isocyanide (10.92 mg, 12.27 pi, 0.10 mmol, 1.0 equiv; [931-53-3]) were added and stirring continued at rt for 2 h. A solution of 4 M HCl in dioxane (0.2 mL) was added and the reaction mixture stirred at rt overnight. Removal of the solvent mixture under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile I water provided 17.5 mg (34%) of the title compound. MS (ISP): 516.2 [M+H]+.

Aufarbeitung

  1. stirringstirring
  2. waitcontinued at rt for 2 h
  3. stirringthe reaction mixture stirred at rt overnight
  4. customRemoval of the solvent mixture
  5. customunder reduced pressure and purification by preparative HPLC on reversed phase
  6. washeluting with a gradient of acetonitrile I water

Quellen und Nachweise

ORD-Eintrag
ord-cef23f7fe806428fb7397ea46f8a11af
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790904B2

Notizen zur Reaktion

Wird geladen…