Triethylamine → Cyclohexanecarboxylic acid [2-chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-[4-(2-Pyrrolidin-1-yl-ethoxy)-phenyl]-amide

HRID 1827537노트

반응식

HRID 1827537 반응식
[CH:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:10][C:11]1[CH:32]=[C:31]([O:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][O:35]2)[CH:30]=[CH:29][C:12]=1[CH2:13][NH:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=[CH:17][CH:16]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:10][C:11]1[CH:32]=[C:31]([O:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][O:35]2)[CH:30]=[CH:29][C:12]=1[CH2:13][N:14]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][N:24]2[CH2:25][CH2:26][CH2:27][CH2:28]2)=[CH:17][CH:16]=1)[C:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:8]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 22137435(2-Chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine

생성물 1

HCID 86760097Cyclohexanecarboxylic acid [2-chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-[4-(2-Pyrrolidin-1-yl-ethoxy)-phenyl]-amide수율 87.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of cyclohexanecarbonyl chloride (990 mg, 6.75 mmol) in methylene chloride (30 mL) was added a mixture of (2-chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine (1.94 g, 4.5 mmol) and triethylamine (1.3 mL, 9.0 mmol) in methylene chloride (15 mL) dropwise. The reaction mixture was stirred at room temperature for 24 hr. The reaction mixture was quenched with saturated aqueous sodium bicarbonate solution and the aqueous solution was washed with methylene chloride. The organic solution was dried (sodium sulfate), filtered and concentrated in vacuo. The crude product was purified by Biotage® chromatography using 5% methanol/methylene chloride to afford the title compound of Step A as an oil (2.12 g). MS 541.3 (M+1)+

후처리

  1. customThe reaction mixture was quenched with saturated aqueous sodium bicarbonate solution
  2. washthe aqueous solution was washed with methylene chloride
  3. dry with materialThe organic solution was dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by Biotage® chromatography

출처 및 근거

ORD 기록
ord-7d3978a5de3d46ecb8664dbe8c84a661
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07053212B2

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