Aluminum(III) Chloride → 3-(2-Amino-6-phenoxy-3,4-dihydro-quinolin-3-yl)-N-cyclohexyl-N-methyl-propionamide

HRID 252465노트

반응식

HRID 252465 반응식
[CH:1]1([N:7]([CH3:30])[C:8](=[O:29])[CH2:9][CH2:10][CH:11]([C:27]#[N:28])[CH2:12][C:13]2[CH:18]=[C:17]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:16]=[CH:15][C:14]=2[NH2:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl-].[Al+3].[Cl-].[Cl-]>C1(C)C=CC=CC=1>[NH2:28][C:27]1[CH:11]([CH2:10][CH2:9][C:8]([N:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH3:30])=[O:29])[CH2:12][C:13]2[C:14](=[CH:15][CH:16]=[C:17]([O:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:18]=2)[N:26]=1

참가 물질

4

반응물 2

HCID 6451240Aluminum(III) ChlorideHCID 672689265-(2-Amino-5-phenoxy-phenyl)-4-cyano-pentanoic acid cyclohexyl-methyl-amide

생성물 1

HCID 594281643-(2-Amino-6-phenoxy-3,4-dihydro-quinolin-3-yl)-N-cyclohexyl-N-methyl-propionamide

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

5-(2-amino-5-phenoxy-phenyl)-4-cyano-pentanoic acid cyclohexyl-methyl-amide (0.20 g, 0.46 mmol) was dissolved in toluene (5 mL), followed by addition of aluminum chloride (0.184 g, 1.38 mmol). The reaction mixture was heated to reflux for 10 minutes and was then allowed to cool to room temperature. The crude reaction mixture was poured into a separatory funnel and partitioned between ethyl acetate and 10% aqueous Na2CO3 solution. The organic layer was washed 2 more times with 10% aqueous Na2CO3 solution and one time with saturated brine solution. The organic layer was dried with anhydrous sodium sulfate and the solvent was removed under reduced pressure to yield a residue which was purified by flash chromatography using chloroform:methanol:triethylamine as the mobile phase to yield the title compound as a residue.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 10 minutes
  3. customThe crude reaction mixture
  4. additionwas poured into a separatory funnel
  5. custompartitioned between ethyl acetate and 10% aqueous Na2CO3 solution
  6. washThe organic layer was washed 2 more times with 10% aqueous Na2CO3 solution and one time with saturated brine solution
  7. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customto yield a residue which
  10. customwas purified by flash chromatography

출처 및 근거

ORD 기록
ord-45b94f456c4d4e74834083ba46a1a30e
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868022B2

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