Potassium Carbonate → 3-ethynyl-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide

HRID 1773473Notes

Reaction equation

HRID 1773473 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[C:9]([CH:31]=[CH:32][C:33]=1[CH3:34])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][N:20]2[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]2)=[C:15]([C:27]([F:30])([F:29])[F:28])[CH:14]=1)=[O:11])(C)C.C(=O)([O-])[O-].[K+].[K+]>CO>[C:6]([C:7]1[CH:8]=[C:9]([CH:31]=[CH:32][C:33]=1[CH3:34])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][N:20]2[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]2)=[C:15]([C:27]([F:28])([F:30])[F:29])[CH:14]=1)=[O:11])#[CH:5]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 689162413-trimethylsilylethynyl-4-methyl-N-[4-((4-methylpiperazin-1-yl)methyl)-3-trifluoromethylphenyl]benzamide

Product 1

HCID 577373983-ethynyl-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The product (1.59 g, 3.3 mmol) obtained from Step 2, potassium carbonate (1.82 g, 13.2 mmol) and 20 ml methanol were mixed in a reactor, and stirred at room temperature under the protection of an inert gas atmosphere for 3 hours. After completion of the reaction, methanol was removed on a rotary evaporator and the mixture was extracted with ethyl acetate and water. The organic layers were combined, washed with a saturated NaCl solution, and dried over anhydrous Na2SO4. The organic solution was concentrated on a rotary evaporator, and the residue was purified by silica gel column chromatography, to give a yellow oily liquid.

Workup

  1. customwas removed on a rotary evaporator
  2. extractionthe mixture was extracted with ethyl acetate and water
  3. washwashed with a saturated NaCl solution
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationThe organic solution was concentrated on a rotary evaporator
  6. customthe residue was purified by silica gel column chromatography
  7. customto give a yellow oily liquid

Sources & evidence

ORD record
ord-adabdf9fd50f4f3e9b612591103fac55
Source dataset
uspto-grants-2016_02
Patent number
US09255107B2

Reaction notes

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