Triethylamine → Methyl 3-[3-[[2-(4-Chlorophenyl)-4-methylthiazol-5-yl]carbonylaminomethyl]piperidin-1-yl]benzoate

HRID 602134

Reaction equation

HRID 602134 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][NH:8][C:9]([C:11]2[S:15][C:14]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[N:13][C:12]=2[CH3:23])=[O:10])[CH2:2]1.[CH3:24][O:25][C:26]([C:28]1[CH:29]=[C:30](OB(O)O)[CH:31]=[CH:32][CH:33]=1)=[O:27].C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([C:14]2[S:15][C:11]([C:9]([NH:8][CH2:7][CH:3]3[CH2:4][CH2:5][CH2:6][N:1]([C:32]4[CH:33]=[C:28]([CH:29]=[CH:30][CH:31]=4)[C:26]([O:25][CH3:24])=[O:27])[CH2:2]3)=[O:10])=[C:12]([CH3:23])[N:13]=2)=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 57572157N-(Piperidin-3-yl methyl)-2-(4-chlorophenyl)-4-methylthiazole-5-carboxamideHCID 671702873-Methoxycarbonylphenylboric acid

Product 1

HCID 67267113Methyl 3-[3-[[2-(4-Chlorophenyl)-4-methylthiazol-5-yl]carbonylaminomethyl]piperidin-1-yl]benzoateYield 37%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

N-(Piperidin-3-yl methyl)-2-(4-chlorophenyl)-4-methylthiazole-5-carboxamide (172 mg, 0.492 mmol), 3-(methoxycarbonyl)phenylboric acid (177 mg, 0.984 mmol) and molecular sieves 4 Å (400 mg) were suspended in dichloromethane (10 mL). To this suspension, copper (II) acetate (188 mg, 0.984 mmol) and triethylamine (0.344 mL, 2.46 mmol) were added and the mixture was stirred at room temperature for 8 hours. Subsequently, the reaction mixture was filtered through Celite, followed by addition of a saturated aqueous sodium bicarbonate solution. The mixture was then extracted with ethyl acetate and the extract washed with brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the residue by silica gel column chromatography (hexane:ethyl acetate=20:1->2:1) gave 88.2 mg (37%) of the desired compound as a colorless powder.

Workup

  1. filtrationSubsequently, the reaction mixture was filtered through Celite
  2. additionfollowed by addition of a saturated aqueous sodium bicarbonate solution
  3. extractionThe mixture was then extracted with ethyl acetate
  4. washthe extract washed with brine
  5. dry with materialby drying over magnesium sulfate and evaporation of the solvent
  6. customPurification of the residue by silica gel column chromatography (hexane:ethyl acetate=20:1->2:1)

Sources & evidence

ORD record
ord-242c2e22b9eb451bb9d6f24bbb2a730a
Source dataset
uspto-grants-2011_03
Patent number
US07902367B2

Linked notes

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