Potassium Carbonate → HCID 67347178, compound

HRID 2199312Notes

Reaction equation

HRID 2199312 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:13])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].Cl[CH2:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][C:17]=1[C:25]([F:28])([F:27])[F:26].[CH3:29][N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.C(#N)C>[CH3:13][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:20](=[O:21])[C:19]2[CH:23]=[CH:24][C:16]([CH2:15][N:33]3[CH2:34][CH2:35][N:30]([CH3:29])[CH2:31][CH2:32]3)=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:18]=2)=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 18690998HCID 18690998, compoundHCID 87356468HCID 87356468, compound

Product 1

HCID 67347178HCID 67347178, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-amino-2-methylbenzoate (500 mg, 2.79 mmol) and TEA (0.78 mL, 5.58 mmol) in dried THF (9 mL) was added 4-(chloromethyl)-3-(trifluoromethyl)benzoyl chloride (714 mg, 2.79 mmol). The reaction mixture was stirred for 5 hours at room temperature after which, it was concentrated under reduced pressure. To a solution of the reaction mixture in acetonitrile (10 mL) were added methyl piperazine (558 mg, 5.58 mmol) and K2CO3 (1.1 g, 8.38 mmol). The reaction mixture was stirred for 8 hours at room temperature. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, celite filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography using (3% to 7% Methanol/CH2C12) as a solvent to afford title compound (820 mg, 63% yield). MS m/z: 464 [M+1].

Workup

  1. concentrationwas concentrated under reduced pressure
  2. stirringThe reaction mixture was stirred for 8 hours at room temperature
  3. customThe reaction mixture was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over MgSO4, celite
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-da41d2f8b30e4f07a88d7ddc9827cc77
Source dataset
uspto-grants-2016_06
Patent number
US09358231B2

Reaction notes

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