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

HRID 350146노트

반응식

HRID 350146 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-78be06b1d96445d792058273c55dfd1f
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179823B1

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