3-Aminopyridine → ethyl 3-[3-phenyl-1-[3-(3-pyridylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionate

HRID 350146ノート

反応式

HRID 350146 の反応式
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][C:8]1[C:9]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:10][N:11]([CH2:13][C:14]2[CH:22]=[CH:21][C:17](C(O)=O)=[CH:16][CH:15]=2)[CH:12]=1)=[O:5])[CH3:2].NC1[CH:31]=[N:32][CH:33]=CC=1.O.[OH:37]N1C2C=CC=CC=2N=N1.CCN=C=N[CH2:52][CH2:53][CH2:54][N:55]([CH3:57])C>O.CN(C)C=O>[C:23]1([C:9]2[C:8]([CH2:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:12][N:11]([CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[C:21]([C:31]([NH:32][C:33]4[CH:57]=[N:55][CH:54]=[CH:53][CH:52]=4)=[O:37])[CH:22]=3)[N:10]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

7

反応物 4

HCID 100093-AminopyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 694228324-[4-(2-ethoxycarbonylethyl)-3-phenyl-1H-pyrazol-1-ylmethyl]benzoic acid

生成物 1

HCID 23024973ethyl 3-[3-phenyl-1-[3-(3-pyridylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionate収率 58.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 4-[4-(2-ethoxycarbonylethyl)-3-phenyl-1H-pyrazol-1-ylmethyl]benzoic acid (400 mg), 3-aminopyridine (160 mg), 1-hydroxybenzotriazole monohydrate (200 mg), WSC (250 mg), and N,N-dimethylformamide (10 ml) was stirred at room temperature for 2.5 days. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium bicarbonate solution, 1 N hydrochloric acid, then, with saturated aqueous sodium chloride solution, and dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and ethyl 3-[3-phenyl-1-[3-(3-pyridylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionate (280 mg, yield: 56%) was obtained as colorless crystals from the fraction eluted with ethyl acetate-methanol (50:1, volume ratio). Melting point: 111–112° C.

後処理

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium bicarbonate solution, 1 N hydrochloric acid
  3. dry with materialwith saturated aqueous sodium chloride solution, and dried (MgSO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-78be06b1d96445d792058273c55dfd1f
出典データセット
uspto-grants-2007_02
特許番号
US07179823B1

反応ノート

読み込み中…