Benzyl Alcohol → Benzyl (2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-carbamate

HRID 604051Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604051
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][N:7]([CH2:15][C:16]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:17]=1C(O)=O)[C:8]1[N:13]=[CH:12][C:11]([Br:14])=[CH:10][N:9]=1.O(P([N:54]=[N+]=[N-])(OC1C=CC=CC=1)=O)C1C=CC=CC=1.[CH2:57]([OH:64])[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1.Cl.[O:66]1[CH2:70]CCC1>C(OCC)(=O)C.C(N(CC)CC)C>[F:35][C:32]([F:34])([F:33])[C:30]1[CH:29]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:37])[F:36])[CH:31]=1)[CH2:6][N:7]([CH2:15][C:16]1[CH:24]=[C:23]([C:25]([F:27])([F:26])[F:28])[CH:22]=[CH:21][C:17]=1[NH:54][C:70](=[O:66])[O:64][CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[C:8]1[N:9]=[CH:10][C:11]([Br:14])=[CH:12][N:13]=1

Komponenten

8

Edukt 5

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 123414Diphenylphosphoryl azideHCID 86626801HCID 86626801, Verbindung

Produkt 1

HCID 86626807Benzyl (2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

2-{[(3,5-Bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-benzoic acid (2.5 g) is dissolved in tetrahydrofuran (25 ml), and thereto are added diphenoxyphosphinylazide (1.34 ml), triethylamine (174 ml) and benzyl alcohol (1.3 ml) and the mixture is heated at 60° C. overnight with stirring. The reaction solution is cooled to room temperature, and thereto are added a 1N-hydrochloric acid and ethyl acetate, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=1:0→9:1→4:1) to give benzyl (2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-carbamate (2.66 g). MS (m/z): 707/709 [M+H]+

Aufarbeitung

  1. temperatureThe reaction solution is cooled to room temperature
  2. customthe mixture is separated
  3. washthe organic layer is washed with a saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=1:0→9:1→4:1)

Quellen und Nachweise

ORD-Eintrag
ord-2c83f9a628a540f2a65ef43c8fe4272a
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906517B2

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