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 2422542Notes

Reaction equation

HRID 2422542 reaction equation
[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]

Participants

5

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-a66f79eb8c6f4d5292a6e787df76a2a0
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

Loading…