Ethyl diazoacetate → ethyl trans-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)pyridazin-4-yl)cyclopropanecarboxylate

HRID 1498790노트

반응식

HRID 1498790 반응식
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:9]=[N:10][CH:11]=[C:12]([CH:14]=[CH2:15])[CH:13]=2)[N:3]=1.[N+](=[CH:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N-]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:9]=[N:10][CH:11]=[C:12]([C@@H:14]3[CH2:15][C@H:18]3[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:13]=2)[N:3]=1

참가 물질

4

반응물 2

HCID 12192Ethyl diazoacetateHCID 867320493-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-5-vinylpyridazine

생성물 1

HCID 86732050ethyl trans-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)pyridazin-4-yl)cyclopropanecarboxylate

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of 3-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-5-vinylpyridazine (23-3, 530 mg, 2.64 mmol 1.0 eq.) in toluene (35 mL) was refluxed under nitrogen. To the reaction mixture was added ethyl diazoacetate (0.50 mL, 4.75 mmol, 1.8 eq.) dropwise. The mixture was refluxed for 2 hours. The solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (20% acetone in hexanes) to afford ethyl trans-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)pyridazin-4-yl)cyclopropanecarboxylate (23-4) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.95 (d, 1H, J=2.0 Hz), 7.71 (d, 1H, J=2.0 Hz), 4.21 (q, 2H, J=7.2 Hz), 2.93 (s, 3H), 2.56 (m, 1H), 2.43 (s, 3H), 2.16 (m, 1H), 1.82 (m, 1H), 1.51 (m, 1H), 1.30 (t, 3H, J=7.2 Hz).

후처리

  1. temperatureThe mixture was refluxed for 2 hours
  2. customThe solvent was removed under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (20% acetone in hexanes)

출처 및 근거

ORD 기록
ord-f4d5f3a69e8844ed9d1dceb76eecec5c
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09200001B2

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