Triethylamine → Rac-3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1h-indol-3-yl]-piperidine-1-carboxylic acid (2-methoxy-phenyl)-amide

HRID 2102712노트

반응식

HRID 2102712 반응식
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)([CH:12]3[CH2:17][CH2:16][CH2:15][NH:14][CH2:13]3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:33][O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[N:41]=[C:42]=[O:43]>ClCCl>[CH3:33][O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[NH:41][C:42]([N:14]1[CH2:15][CH2:16][CH2:17][CH:12]([C:6]2([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)[C:5]3[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=3)[NH:8][C:7]2=[O:11])[CH2:13]1)=[O:43]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 69695Benzene, 1-isocyanato-2-methoxy-HCID 57803070Rac-6-chloro-3-(3-chloro-benzyl)-3-piperidin-3-yl-1,3-dihydro-indol-2-one

생성물 1

HCID 11998416Rac-3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1h-indol-3-yl]-piperidine-1-carboxylic acid (2-methoxy-phenyl)-amide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of rac-6-chloro-3-(3-chloro-benzyl)-3-piperidin-3-yl-1,3-dihydro-indol-2-one (50 mg, 0.13 mmol) (from Example 25a supra) in dichloromethane (3 mL) was added triethylamine (20 mg, 0.19 mmol) (Aldrich), followed by the addition of 2-methoxyphenyl isocyanate (24 mg, 0.16 mmol) (Aldrich). The mixture was stirred at room temperature for 30 mins. The mixture was partitioned between dichlormethane and water. The aqueous layer was extracted with dichlormethane. The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated. The residue was purified by chromatography to give rac-3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-piperidine-1-carboxylic acid (2-methoxy-phenyl)-amide as a white solid. (Yield 45 mg, 64%).

후처리

  1. customThe mixture was partitioned between dichlormethane and water
  2. extractionThe aqueous layer was extracted with dichlormethane
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography

출처 및 근거

ORD 기록
ord-bc20a57b52f74161882d7e97ccd35cad
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576082B2

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