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2-Aminopyridine → ethyl 3-[3-phenyl-1-[3-(2-pyridylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionate

HRID 350142
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반응식

HRID 350142 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]=CC(C(O)=O)=[CH:16][CH:15]=2)[CH:12]=1)=[O:5])[CH3:2].N[C:30]1[CH:35]=CC=CN=1.O.[OH:37]N1C2C=CC=CC=2N=N1.[CH3:47][CH2:48][N:49]=[C:50]=[N:51][CH2:52][CH2:53][CH2:54]N(C)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:54]=[C:53]([C:52]([NH:51][C:50]4[CH:30]=[CH:35][CH:47]=[CH:48][N:49]=4)=[O:37])[CH:22]=3)[N:10]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 104392-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 23024837ethyl 3-[3-phenyl-1-[3-(2-pyridylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionate수율 41.6%

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), 2-aminopyridine (120 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 sodium chloride solution, and dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and ethyl 3-[3-phenyl-1-[3-(2-pyridylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionate (200 mg, yield: 40%) was obtained as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (5:1, volume ratio).

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 sodium chloride solution, and dried (MgSO4)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-254ca7dc27c349f8b3a0489d8583fb47
출처 데이터셋
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07179823B1

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