Water → 4-(3-Chloro-phenyl)-6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-1-cyclopropylmethyl-1H-quinolin-2-one

HRID 2298987Notes

Reaction equation

HRID 2298987 reaction equation
C([Si](C)(C)[C:6]1[N:10]([CH3:11])[C:9]([C:12]([C:36]2[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=2)([OH:35])[C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]([CH2:23][CH:24]2[CH2:26][CH2:25]2)[C:18](=[O:27])[CH:17]=[C:16]3[C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=2)=[CH:8][N:7]=1)(C)(C)C.O>C1COCC1.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:34][C:30]1[CH:29]=[C:28]([C:16]2[C:15]3[C:20](=[CH:21][CH:22]=[C:13]([C:12]([C:36]4[CH:37]=[CH:38][C:39]([Cl:42])=[CH:40][CH:41]=4)([OH:35])[C:9]4[N:10]([CH3:11])[CH:6]=[N:7][CH:8]=4)[CH:14]=3)[N:19]([CH2:23][CH:24]3[CH2:26][CH2:25]3)[C:18](=[O:27])[CH:17]=2)[CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 2

HCID 962WaterHCID 183790136-[[2-(tert-butyl-dimethyl-silanyl)-3-methyl-3H-imidazol-4-yl]-(4-chloro-phenyl)-hydroxy-methyl]-4-(3-chloro-phenyl)-1-cyclopropylmethyl-1H-quinolin-2-one

Product 1

HCID 99149464-(3-Chloro-phenyl)-6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-1-cyclopropylmethyl-1H-quinolin-2-oneYield 68%

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-[[2-(tert-butyl-dimethyl-silanyl)-3-methyl-3H-imidazol-4-yl]-(4-chloro-phenyl)-hydroxy-methyl]-4-(3-chloro-phenyl)-1-cyclopropylmethyl-1H-quinolin-2-one (4.24 g crude) in THF (100 mL) was treated with tetrabutylammonium chloride (1 M in THF, 10.0 mmol). The reaction mixture was stirred at room temperature for 12 hours, poured into H2O (200 mL), and extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with 1N HCl (100 mL), aqueous NaHCO3 (100 mL), and brine (100 mL), dried (MgSO4), filtered, and concentrated in vacuo to give a light green foam. Purification by flash column chromatography (silica, EtOAc:pet. ether:NH4OH 1:1:.01) gave 4-(3-Chloro-phenyl)-6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-1-cyclopropylmethyl-1H-quinolin-2-one (2.3 g, 68%) as a light yellow solid.

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washThe combined organic extracts were washed with 1N HCl (100 mL), aqueous NaHCO3 (100 mL), and brine (100 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a light green foam
  7. customPurification by flash column chromatography (silica, EtOAc:pet. ether:NH4OH 1:1:.01)

Sources & evidence

ORD record
ord-9a78fecb237e4254a72a71eefadcc109
Source dataset
uspto-grants-2002_12
Patent number
US06495564B1

Reaction notes

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