Sodium Carbonate → methyl 2-[2-(5-bromo-1-methyl-1H-pyrazol-4-yl)-2-oxoethyl]-2-formylhydrazinecarboxylate

HRID 1907213노트

반응식

HRID 1907213 반응식
COC1C=CC(CN[CH:9]=[N:10][NH:11][C:12]([O:14][CH3:15])=[O:13])=CC=1.Br[CH2:19][C:20]([C:22]1[CH:23]=[N:24][N:25]([CH3:28])[C:26]=1[Br:27])=[O:21].C(=O)([O-])[O-:30].[Na+].[Na+].C(N(CC)C(C)C)(C)C>C(#N)C.O>[Br:27][C:26]1[N:25]([CH3:28])[N:24]=[CH:23][C:22]=1[C:20](=[O:21])[CH2:19][N:10]([CH:9]=[O:30])[NH:11][C:12]([O:14][CH3:15])=[O:13]

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 866697172-bromo-1-(5-bromo-1-methyl-1H-pyrazol-4-yl)ethanoneHCID 178502533HCID 178502533, 화합물

생성물 1

HCID 86669721methyl 2-[2-(5-bromo-1-methyl-1H-pyrazol-4-yl)-2-oxoethyl]-2-formylhydrazinecarboxylate수율 27.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

Methyl 2-{[(4-methoxybenzyl)amino]methylene}hydrazinecarboxylate (3.28 g, 13.8 mmol), 2-bromo-1-(5-bromo-1-methyl-1H-pyrazol-4-yl)ethanone (3.90 g, 13.8 mmol) and sodium carbonate (1.16 g, 13.8 mmol) were combined in a mixture of N,N-diisopropylethylamine (99.5%, 2.30 mL, 13.8 mmol) and acetonitrile (30 mL). The reaction was heated at 80° C. for 18 hours, at which time water was added, and heated was continued for 10 minutes. After removal of solvent in vacuo, the aqueous residue was partitioned between water and ethyl acetate (100 mL). The aqueous layer was extracted with ethyl acetate (4×100 mL), and the combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification using silica gel chromatography (Gradient: 0% to 100% ethyl acetate in heptane) provided the product (1.20 g), contaminated with some impurities. This material was taken directly to the following step. LCMS m/z 319.0 (M+1). 1H NMR (400 MHz, CD3OD) δ, product peaks: 3.74 (s, 3H), 3.92 (s, 3H), 4.82 (br s, 2H), 8.14 (s, 1H), 8.24 (s, 1H).

후처리

  1. additionwas added
  2. temperatureheated
  3. customAfter removal of solvent in vacuo
  4. customthe aqueous residue was partitioned between water and ethyl acetate (100 mL)
  5. extractionThe aqueous layer was extracted with ethyl acetate (4×100 mL)
  6. dry with materialthe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification

출처 및 근거

ORD 기록
ord-d30d833e49df4e8c8823dac5d7b871a4
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598155B2

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