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

HRID 2422530Notes

Reaction equation

HRID 2422530 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[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=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>[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[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:29][C:30]([C:34]#[N:35])=[N:31]3)=[CH:26][CH:25]=2)[CH:22]=1)([C:14]([F:15])([F:17])[F:16])[CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66791323(S)-1-{1-[(2-cyano-4-phenylquinolin-7-yl)methyl]-1H-1,2,3-triazol-4-yl}-1-(trifluoromethyl)propyl 4-nitrobenzoate

Product 1

HCID 25056110(S)-7-({4-[1-hydroxy-1-(trifluoromethyl)propyl]-1H-1,2,3-triazol-1-yl}methyl)-4-phenylquinoline-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-1-{1-[(2-cyano-4-phenylquinolin-7-yl)methyl]-1H-1,2,3-triazol-4-yl}-1-(trifluoromethyl)propyl 4-nitrobenzoate (200 mg, 0.34 mmol) in THF (6 mL) was added lithium hydroxide IM (1.7 mL, 1.7 mmol). The mixture was stirred at room temperature for 1 h and quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification on silica gel (eluting with acetone/dichloromethane, 1:9) gave the title compound. MS (+ESI): 438 (M+H)+.

Workup

  1. customquenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification on silica gel (eluting with acetone/dichloromethane, 1:9)

Sources & evidence

ORD record
ord-a8727b32b110444a886ab602989dc967
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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