Cesium carbonate → 5-ethyl-1-(2-methoxyethyl)-4-nitro-1H-pyrazole-3-carboxamide

HRID 348412

반응식

HRID 348412 반응식
[CH2:1]([C:3]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([C:11]([NH2:13])=[O:12])[NH:5][N:4]=1)[CH3:2].[CH3:14][O:15][CH2:16][CH2:17]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:1]([C:3]1[N:4]([CH2:17][CH2:16][O:15][CH3:14])[N:5]=[C:6]([C:11]([NH2:13])=[O:12])[C:7]=1[N+:8]([O-:10])=[O:9])[CH3:2]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 178438045HCID 178438045, 화합물

생성물 1

HCID 112187175-ethyl-1-(2-methoxyethyl)-4-nitro-1H-pyrazole-3-carboxamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 3-ethyl-4-nitro-1H-pyrazole-5-carboxamide (WO, 9849166), (1.7 g, 8.8 mmol), 2-bromoethyl methyl ether (0.85 ml, 8.85 mmol) and cesium carbonate (2.9 g, 9.0 mmol) in N,N-dimethylformamide (20 ml) was stirred at room temperature for 20 hours. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate (125 ml) and brine (100 ml). The phases were separated, and the organic layer was dried (Na2SO4), and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel, using ethyl acetate:methanol (97:3) as eluant to afford the title compound of preparation 1, 831 mg,

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate (125 ml) and brine (100 ml)
  3. customThe phases were separated
  4. dry with materialthe organic layer was dried (Na2SO4)
  5. customevaporated under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel
  7. customto afford

출처 및 근거

ORD 기록
ord-ba2e88d262594634be8af0fd568efffb
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176311B2

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