Benzoyl chloride → n-[[4-[[(2-Pyridinylmethyl)amino]methyl]phenyl]methyl]-n-(5,6,7,8-tetrahydro-8-quinolinyl)-benzamide

HRID 351183노트

반응식

HRID 351183 반응식
[N+](C1C=CC=CC=1S([N:13]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1)[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][NH:22][CH:23]2[C:32]3[N:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH2:26][CH2:25][CH2:24]2)=[CH:17][CH:16]=1)(=O)=O)([O-])=O.C(N(CC)CC)C.[C:47](Cl)(=[O:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>C(Cl)Cl>[N:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[CH2:33][NH:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][N:22]([CH:23]2[C:32]3[N:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH2:26][CH2:25][CH2:24]2)[C:47](=[O:54])[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[CH:19][CH:20]=1

참가 물질

5

반응물 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 22018658N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-N'-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

생성물 1

HCID 22256389n-[[4-[[(2-Pyridinylmethyl)amino]methyl]phenyl]methyl]-n-(5,6,7,8-tetrahydro-8-quinolinyl)-benzamide수율 118.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a pre-cooled (ice bath) solution of N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (201 mg, 0.37 mmol) and triethylamine (80 μl, 0.55 mmol) in anhydrous CH2Cl2 (4 mL) was added a solution of benzoylchloride (54 μl, 0.46 mmol) in anhydrous CH2Cl2 (0.5 mL) and the reaction mixture was allowed to stir at room temperature for 18 hours and then concentrated. The residue was diluted with ethylacetate (300 mL), washed with sat. aqueous NaHCO3 then brine, dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica gel (1.5×20 cm, 50:50 EtOAc/CH2Cl2) to give the desired amide (203 mg, 85%) as a yellow oil.

후처리

  1. concentrationconcentrated
  2. additionThe residue was diluted with ethylacetate (300 mL)
  3. washwashed with sat. aqueous NaHCO3
  4. dry with materialbrine, dried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel (1.5×20 cm, 50:50 EtOAc/CH2Cl2)

출처 및 근거

ORD 기록
ord-797727f2344f4e31903f00544bee8a3d
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183273B2

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