Potassium Carbonate → 4-(3-Chloro-phenyl)-6-[(4-chloro-phenyl)-(3-methyl-3H-imidazol-4-yl)-[1,2,3]triazol-2-yl-methyl]-1-cyclopropylmethyl-1H-quinolin-2-one

HRID 2298990Notes

Reaction equation

HRID 2298990 reaction equation
Cl[C:2]([C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)([C:25]1[N:26]([CH3:30])[CH:27]=[N:28][CH:29]=1)[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH:14]1[CH2:16][CH2:15]1)[C:8](=[O:17])[CH:7]=[C:6]2[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1.C([O-])([O-])=O.[K+].[K+].[NH:44]1[CH:48]=[CH:47][N:46]=[N:45]1>CN(C=O)C.O>[Cl:24][C:20]1[CH:19]=[C:18]([C:6]2[C:5]3[C:10](=[CH:11][CH:12]=[C:3]([C:2]([C:31]4[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=4)([C:25]4[N:26]([CH3:30])[CH:27]=[N:28][CH:29]=4)[N:45]4[N:46]=[CH:47][CH:48]=[N:44]4)[CH:4]=3)[N:9]([CH2:13][CH:14]3[CH2:16][CH2:15]3)[C:8](=[O:17])[CH:7]=2)[CH:23]=[CH:22][CH:21]=1.[Cl:24][C:20]1[CH:19]=[C:18]([C:6]2[C:5]3[C:10](=[CH:11][CH:12]=[C:3]([C:2]([C:31]4[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=4)([C:25]4[N:26]([CH3:30])[CH:27]=[N:28][CH:29]=4)[N:44]4[CH:48]=[CH:47][N:46]=[N:45]4)[CH:4]=3)[N:9]([CH2:13][CH:14]3[CH2:16][CH2:15]3)[C:8](=[O:17])[CH:7]=2)[CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 183790276-[Chloro-(4-chloro-phenyl)-(3-methyl-3H-imidazol-4-yl)-methyl]-4-(3-chloro-phenyl)-1-cyclopropylmethyl-1H-quinolin-2-oneHCID 178418936HCID 178418936, compound

Product 2

HCID 183790164-(3-Chloro-phenyl)-6-[(4-chloro-phenyl)-(3-methyl-3H-imidazol-4-yl)-[1,2,3]triazol-1-yl-methyl]-1-cyclopropylmethyl-1H-quinolin-2-oneYield 9%HCID 183790244-(3-Chloro-phenyl)-6-[(4-chloro-phenyl)-(3-methyl-3H-imidazol-4-yl)-[1,2,3]triazol-2-yl-methyl]-1-cyclopropylmethyl-1H-quinolin-2-oneYield 34%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 6-[Chloro-(4-chloro-phenyl)-(3-methyl-3H-imidazol-4-yl)-methyl]-4-(3-chloro-phenyl)-1-cyclopropylmethyl-1H-quinolin-2-one (0.094 g, 0.17 mmol) in DMF (7 mL) was treated with K2CO3 (0.24 g, 0.17 mmol) and 1,2,3-triazole (0.061 mL, 1.03 mmol). The reaction mixture was heated at 80° C. for 12 hours, diluted with H2O (2 mL), and extracted with EtOAc (2 mL). The organic phase was washed with brine (2 mL), dried (MgSO4), filtered, and concentrated in vacuo to give a yellow oil. Purification by radio chromatography (silica, CH2Cl2:CH3OH:NH4OH 98:1.8:0.2) gave 4-(3-Chloro-phenyl)-6-[(4-chloro-phenyl)-(3-methyl-3H-imidazol-4-yl)-[1,2,3]triazol-2-yl-methyl]-1-cyclopropylmethyl-1H-quinolin-2-one (34 mg, 34%) and 4-(3-Chloro-phenyl)-6-[(4-chloro-phenyl)-(3-methyl-3H-imidazol-4-yl)-[1,2,3]triazol-1-yl-methyl]-1-cyclopropylmethyl-1H-quinolin-2-one (9.5 mg, 9%) as yellow oils.

Workup

  1. extractionextracted with EtOAc (2 mL)
  2. washThe organic phase was washed with brine (2 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a yellow oil
  7. customPurification by radio chromatography (silica, CH2Cl2:CH3OH:NH4OH 98:1.8:0.2)

Sources & evidence

ORD record
ord-50316636f3414e949ef776dff5936827
Source dataset
uspto-grants-2002_12
Patent number
US06495564B1

Reaction notes

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