Lithium Hydroxide → (S)-7-({4-[1-hydroxy-1-(trifluoromethyl)propyl]-1H-1,2,3-triazol-1-yl}methyl)-4-(2-methyl-1,3-oxazol-4-yl)quinoline-2-carbonitrile

HRID 2422542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2422542
[N+](C1C=CC(C([O:10][C@@:11]([C:18]2[N:19]=[N:20][N:21]([CH2:23][C:24]3[CH:33]=[C:32]4[C:27]([C:28]([C:36]5[N:37]=[C:38]([CH3:41])[O:39][CH:40]=5)=[CH:29][C:30]([C:34]#[N:35])=[N:31]4)=[CH:26][CH:25]=3)[CH:22]=2)([C:14]([F:17])([F:16])[F:15])[CH2:12][CH3:13])=O)=CC=1)([O-])=O.[OH-].[Li+]>C1COCC1.C(OCC)(=O)C>[OH:10][C@@:11]([C:18]1[N:19]=[N:20][N:21]([CH2:23][C:24]2[CH:33]=[C:32]3[C:27]([C:28]([C:36]4[N:37]=[C:38]([CH3:41])[O:39][CH:40]=4)=[CH:29][C:30]([C:34]#[N:35])=[N:31]3)=[CH:26][CH:25]=2)[CH:22]=1)([C:14]([F:16])([F:15])[F:17])[CH2:12][CH3:13]

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 66791318(S)-1-(1-{[2-cyano-4-(2-methyl-1,3-oxazol-4-yl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate

Produkt 1

HCID 66790903(S)-7-({4-[1-hydroxy-1-(trifluoromethyl)propyl]-1H-1,2,3-triazol-1-yl}methyl)-4-(2-methyl-1,3-oxazol-4-yl)quinoline-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (S)-1-(1-{[2-cyano-4-(2-methyl-1,3-oxazol-4-yl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate (36 mg, 0.06 mmol) in THF (1.4 mL) was added lithium hydroxide 2M (150 uL, 0.3 mmol). The mixture was stirred at room temperature for 2 h. The reaction mixture was then diluted with ethyl acetate, washed with an ammonium chloride solution, brine, dried over MgSO4, filtered and concentrated to yield the title compound. The crude residue was purified by flash chromatography (10% acetone-90% dichloromethane) to give the desired product. 1H NMR (400 MHz, acetone-d6): δ 8.9 (d, 1H), 8.73 (s, 1H), 8.24 (d, 2H), 8.11 (s, 1H), 7.80 (d, 1H), 6.02 (s, 2H), 5.49 (s, 1H), 2.6 (s, 3H), 2.35 (m, 1H), 2.05 (m, 1H), 0.86 (t, 3H).

Aufarbeitung

  1. washwashed with an ammonium chloride solution, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a66f79eb8c6f4d5292a6e787df76a2a0
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960409B2

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