1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 6-(4-Biphenylylmethoxy)-N-(2-piperidinoethyl)nicotinamide

HRID 1356468노트

반응식

HRID 1356468 반응식
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[C:10]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:15]=[CH:14][C:13]([CH2:16][O:17][C:18]2[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][N:19]=2)=[CH:12][CH:11]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(#N)C.C(=O)([O-])[O-].[K+].[K+].C(N(CC)CC)C.C1COCC1>[C:10]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:15]=[CH:14][C:13]([CH2:16][O:17][C:18]2[CH:26]=[CH:25][C:21]([C:22]([NH:1][CH2:2][CH2:3][N:4]3[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]3)=[O:23])=[CH:20][N:19]=2)=[CH:12][CH:11]=1

참가 물질

9

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 33944N-(2-Aminoethyl)piperidineHCID 757711-HydroxybenzotriazoleHCID 178174806-(4-Biphenylylmethoxy)nicotinic Acid

생성물 1

HCID 185083446-(4-Biphenylylmethoxy)-N-(2-piperidinoethyl)nicotinamide수율 66.1%

시약·촉매·용매 4

HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매HCID 11430Potassium Carbonate용매

실험 절차

To a solution of 1-(2-aminoethyl)piperidine (260 mg) in acetonitrile (5 ml)/THF (10 ml) were added 6-(4-biphenylylmethoxy)nicotinic acid (500 mg), WSC (380 mg), HOBt (260 mg), and triethylamine (0.7 ml) at room temperature. After stirring at room temperature for 36 hr, the reaction mixture was diluted with 5% aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride sequentially, dried, and concentrated. The residue was purified by alumina column chromatography (THF) and recrystallized from ethyl acetate to obtain the titled compound (450 mg).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride sequentially
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by alumina column chromatography (THF)
  6. customrecrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-48d9ef30a4504ecbb83fa0f4c8e5be50
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586475B1

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