Dimethylformamide → 2-chloro-5-(5-methyl-1H-pyrazol-3-yl)-benzoic acid methyl ester

HRID 1988371노트

반응식

HRID 1988371 반응식
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([C:10](=O)[CH3:11])[CH:7]=[CH:6][C:5]=1[Cl:13].CO[C:17](OC)([N:19](C)C)[CH3:18].C[N:25](C)C=O>CN(C)C(=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[C:17]([CH3:18])[NH:19][N:25]=2)[CH:7]=[CH:6][C:5]=1[Cl:13]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 58818179Methyl 5-acetyl-2-chlorobenzoate

생성물 1

HCID 588181962-chloro-5-(5-methyl-1H-pyrazol-3-yl)-benzoic acid methyl ester

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

A solution of 5-acetyl-2-chloro-benzoic acid methyl ester (1.58 g, 7.5 mmol) and N,N-dimethylacetamide dimethylacetal in N,N-dimethylformamide and N,N-dimethylacetamide was stirred at 90° C. for 3 h. The mixture was cooled to room temperature and concentrated in vacuo. The residue was diluted with ethanol (18 mL) and tetrahydrofuran (2 mL). Hydrazine hydrate (0.34 mL) was added and the mixture was stirred at room temperature for 16 h. The mixture was concentrated in vacuo. The residue was purified by flash column chromatography (gradient 0-10% methanol-ethyl acetate) to afford the title compound (1.0 g).

후처리

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with ethanol (18 mL) and tetrahydrofuran (2 mL)
  3. additionHydrazine hydrate (0.34 mL) was added
  4. concentrationThe mixture was concentrated in vacuo
  5. customThe residue was purified by flash column chromatography (gradient 0-10% methanol-ethyl acetate)

출처 및 근거

ORD 기록
ord-b3b383b9515748fead96a2b84a27ac18
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07553972B2

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