Ethyl Acetate → 4-{3-[2-chloro-4-(4-cyano-1-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-6-trifluoromethyl-phenoxy]-propyl}-piperazine-1-carboxylic acid tert-butyl ester

HRID 2079558Notes

Reaction equation

HRID 2079558 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16]Br)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:18][C:19]1[CH:20]=[C:21]([C:30]2[N:35]=[C:34]([C:36]#[N:37])[C:33]3[N:38]=[CH:39][N:40]([CH3:41])[C:32]=3[CH:31]=2)[CH:22]=[C:23]([C:26]([F:29])([F:28])[F:27])[C:24]=1[OH:25].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(#N)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][O:25][C:24]2[C:23]([C:26]([F:27])([F:28])[F:29])=[CH:22][C:21]([C:30]3[N:35]=[C:34]([C:36]#[N:37])[C:33]4[N:38]=[CH:39][N:40]([CH3:41])[C:32]=4[CH:31]=3)=[CH:20][C:19]=2[Cl:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 15946517tert-Butyl 4-(3-bromopropyl)piperazine-1-carboxylateHCID 1361890446-(3-chloro-4-hydroxy-5-trifluoromethyl-phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile

Product 1

HCID 576575484-{3-[2-chloro-4-(4-cyano-1-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-6-trifluoromethyl-phenoxy]-propyl}-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

4-(3-Bromo-propyl)-piperazine-1-carboxylic acid tert-butyl ester (172 mg) was added to a mixture of 6-(3-chloro-4-hydroxy-5-trifluoromethyl-phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile (165 mg) and potassium carbonate (130 mg) in acetonitrile (15 ml). The mixture was refluxed for 4 hours, then ethyl acetate (50 ml) and water (30 ml) were added and the organic layer was washed with brine, then dried over sodium sulfate, filtered and concentrated under reduced pressure to afford a crude product, 4-{3-[2-chloro-4-(4-cyano-1-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-6-trifluoromethyl-phenoxy]-propyl}-piperazine-1-carboxylic acid tert-butyl ester.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. washthe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-396575f2ba024ccbb961187e09558a75
Source dataset
uspto-grants-2011_04
Patent number
US07932251B2

Reaction notes

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