1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 6-(4-Biphenylylmethoxy)-N-[2-(N,N-dimethylamino)ethyl]nicotinamide

HRID 1356469ノート

反応式

HRID 1356469 の反応式
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].[C:7]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:12]=[CH:11][C:10]([CH2:13][O:14][C:15]2[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][N:16]=2)=[CH:9][CH:8]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(#N)C.C(N(CC)CC)C.C1COCC1>[C:7]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:12]=[CH:11][C:10]([CH2:13][O:14][C:15]2[CH:23]=[CH:22][C:18]([C:19]([NH:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])=[O:20])=[CH:17][N:16]=2)=[CH:9][CH:8]=1

参加物

8

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66053N,N-DimethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 178174806-(4-Biphenylylmethoxy)nicotinic Acid

生成物 1

HCID 185083656-(4-Biphenylylmethoxy)-N-[2-(N,N-dimethylamino)ethyl]nicotinamide収率 72.3%

試薬・触媒・溶媒 3

HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

実験手順

To a solution of N,N-dimethylethylenediamine (160 mg) in acetonitrile (5 ml)/THF (10 ml) were added 6-(4-biphenylylmethoxy)nicotinic acid (450 mg), WSC (340 mg), HOBt (230 mg), and triethylamine (0.7 ml) at room temperature. After stirring at room temperature for 12 hr, the reaction mixture was diluted with 10% aqueous potassium carbonates and extracted with ethyl acetate/THF. The organic layer was washed with water and saturated aqueous sodium chloride, dried, and concentrated. The residue was purified by alumina column chromatography (eluent; THF) and recrystallized from ethyl acetate/diisopropyl ether to obtain the titled compound (400 mg).

後処理

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

出典と根拠

ORDレコード
ord-c827072e90d04ce1a1706c8ef7d59cc9
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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