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

HRID 604044Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604044
[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=[N+]=[N-])([O:47][C:48]1[CH:53]=CC=CC=1)=O)C1C=CC=CC=1.C([N:59]([CH2:62]C)CC)C.Cl.[O:65]1CCCC1>C(OCC)(=O)C.C(O)C>[F:34][C:32]([F:35])([F:33])[C:30]1[CH:29]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:36])[F:37])[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:59][C:62](=[O:65])[O:47][CH2:48][CH3:53])[C:8]1[N:13]=[CH:12][C:11]([Br:14])=[CH:10][N:9]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 86626801HCID 86626801, Verbindung

Produkt 1

HCID 86626802Ethyl (2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

2-{[(3,5-Bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-benzoic acid (1 g) is dissolved in tetrahydrofuran (10 ml), and thereto are added diphenoxyphosphinylazide (540 μl), triethylamine (695 μl) and ethanol (6 ml) and the mixture is heated at 60° C. for 3 days with stirring. The reaction solution is cooled to room temperature, and thereto are added 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→4:1→chloroform:methanol=4:1) to give ethyl (2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-carbamate (660 mg). MS (m/z): 645/647 [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→4:1→chloroform:methanol=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-56d2bc713cf34beaa51249e36b3dc6cc
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906517B2

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