Potassium Carbonate → HCID 67347178、化合物

HRID 709303ノート

反応式

HRID 709303 の反応式
[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]

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 18690998Ethyl 5-amino-2-methylbenzoateHCID 87356468HCID 87356468、化合物

生成物 1

HCID 67347178HCID 67347178、化合物収率 63.4%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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/CH2Cl2) as a solvent to afford title compound (820 mg, 63% yield). MS m/z: 464 [M+1].

後処理

  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

出典と根拠

ORDレコード
ord-60f6154566764cdc8402ba0e7afbc58c
出典データセット
uspto-grants-2015_11
特許番号
US09180127B2

反応ノート

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