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

HRID 1356468ノート

反応式

HRID 1356468 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒HCID 11430Potassium Carbonate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-48d9ef30a4504ecbb83fa0f4c8e5be50
出典データセット
uspto-grants-2003_07
特許番号
US06586475B1

反応ノート

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