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Diisopropylethylamine → 6-Oxo-1-(2-trimethylsilanyl-ethoxymethyl)-1,6-dihydro-pyridazine-4-carboxylic acid ethyl ester

HRID 500538
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HRID 500538 반응식
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][NH:9][C:10](=[O:12])[CH:11]=1)=[O:5])[CH3:2].C(N(C(C)C)CC)(C)C.Cl[CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28]>CN(C)C=O.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:10](=[O:12])[CH:11]=1)=[O:5])[CH3:2]
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참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 12376258Ethyl 6-oxo-1,6-dihydropyridazine-4-carboxylate

생성물 1

HCID 248517026-Oxo-1-(2-trimethylsilanyl-ethoxymethyl)-1,6-dihydro-pyridazine-4-carboxylic acid ethyl ester수율 53.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매
HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

The title compound from Example 18.4 (0.90 g, 5.35 mmol) was stirred in dimethylformamide (20 mL) and diisopropyl ethylamine (1.39 mL, 8.025 mmol) at 0° C. and (2-chloromethoxy-ethyl)-trimethyl-silane (1.88 mL, 10.70 mmol) was added and the reaction was allowed to continue to stir at 0° C. for 2 hours and then overnight at r.t. The reaction mixture was diluted with EtOAc and washed with water and brine. The organic phase was dried over sodium sulfate, filtered and concentrated onto silica gel. The product was purified by column chromatography (0-20% EtOAc/hexanes) to afford the title compound as a clear oil (0.85 g, 53%).

후처리

  1. customovernight
  2. customat r.t
  3. washwashed with water and brine
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated onto silica gel
  7. customThe product was purified by column chromatography (0-20% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-56de719ec7044f52a82a8837ab42c978
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07772235B2

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