Potassium Carbonate → HCID 117840032, compound

HRID 1520263Notes

Reaction equation

HRID 1520263 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:15][C:16]2[CH:32]=[CH:31][C:19]([C:20]([N:22]3[CH2:27][CH2:26][CH2:25][C@@H:24]([C:28]([OH:30])=[O:29])[CH2:23]3)=[O:21])=[CH:18][CH:17]=2)[CH2:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[C:4]([CH3:33])[CH:3]=1.[C:34]([C:36]1[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=1)#[N:35].C(=O)([O-])[O-].[K+].[K+]>COCCOC.O>[C:34]([C:36]1[CH:41]=[CH:40][C:39]([C:2]2[CH:7]=[CH:6][C:5]([CH:8]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([C:20]([N:22]4[CH2:27][CH2:26][CH2:25][C@@H:24]([C:28]([OH:30])=[O:29])[CH2:23]4)=[O:21])=[CH:31][CH:32]=3)[CH2:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[C:4]([CH3:33])[CH:3]=2)=[CH:38][CH:37]=1)#[N:35]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 117840136(3R)-1-(4-((1-(4-bromo-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoyl)piperidine-3-carboxylic acid

Product 1

HCID 117840032HCID 117840032, compoundYield 17.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To (3R)-1-(4-((1-(4-bromo-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoyl)piperidine-3-carboxylic acid (42 mg) was added a solution of 4-cyanophenylboronic acid (24 mg) in DME (0.5 mL), polymer-supported triphenylphosphinepalladium(0) (0.1 mg), and a solution of potassium carbonate (16 mg) in water (0.2 mL), and the mixture was stirred at 80° C. overnight. The reaction solution was passed through a filter, and washed twice with THF (2 mL). The solvent was evaporated from the obtained solution by an air blowing apparatus. The residue was purified by HPLC (C18, mobile phase: water/acetonitrile (0.1% TFA-containing system)), and the solvent was evaporated from the obtained solution by an air blowing apparatus. The residue was purified by HPLC (C18, mobile phase: water/acetonitrile (10 mM ammonium acetate-containing system)) to give the title compound (7.8 mg).

Workup

  1. washwashed twice with THF (2 mL)
  2. customThe solvent was evaporated from the obtained solution by an air
  3. customThe residue was purified by HPLC (C18, mobile phase: water/acetonitrile (0.1% TFA-containing system))
  4. customthe solvent was evaporated from the obtained solution by an air
  5. customThe residue was purified by HPLC (C18, mobile phase: water/acetonitrile (10 mM ammonium acetate-containing system))

Sources & evidence

ORD record
ord-53bef77e842a496b8322dba50ccedf7a
Source dataset
uspto-grants-2015_07
Patent number
US09073864B2

Reaction notes

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