Acetic Acid → HCID 44555440, 화합물

HRID 446762

반응식

HRID 446762 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:13][CH:12]2[C:14]([NH:16][NH2:17])=[O:15])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH:18]1[C:27]2[CH:26]=[CH:25][CH:24]=[C:23]([CH:28]=O)[C:22]=2[CH:21]=[CH:20][N:19]=1.CC(O)=O>C(O)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:13][CH:12]2[C:14]([NH:16]/[N:17]=[CH:28]/[C:23]2[CH:24]=[CH:25][CH:26]=[C:27]3[C:22]=2[CH:21]=[CH:20][N:19]=[CH:18]3)=[O:15])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 5891992-(4-tert-Butylphenyl)cyclopropanecarbohydrazideHCID 7016853Isoquinoline-5-carboxaldehyde

생성물 1

HCID 44555440HCID 44555440, 화합물수율 50.1%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
90 °C

실험 절차

To a room temperature solution of 2-(4-tert-butylphenyl)cyclopropanecarbohydrazide (200 mg, 0.86 mmol) in ethanol (10 mL) were added isoquinoline-5-carbaldehyde (162 mg, 1.0 mmol) and a catalytic amount of glacial AcOH (0.4 mL) under an inert atmosphere. The reaction mixture was then stirred at 90° C. for 4 h, concentrated in vacuo, and the residue was then dissolved in DCM (50 mL). The organic layer was washed with saturated NaHCO3 solution (15 mL) and brine (15 mL). The organic layer was then separated, dried over anhydrous Na2SO4, filtered and evaporated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography eluting with 1% MeOH in dichloromethane to afford (E)-2-(4-tert-butylphenyl)-N′-(isoquinolin-5-ylmethylene) cyclopropanecarbohydrazide (160 mg, 50%) as a white solid. 1H NMR (500 MHz, d6-DMSO): δ 11.60 (s, 1H), 9.38 (s, 1H), 8.71-8.56 (m, 2H), 8.25-8.12 (m, 2H), 8.11-7.99 (m, 2H), 7.39-7.29 (m, 2H), 7.19-7.06 (m, 2H), 2.41-2.33 (m, 1H), 1.95-1.90 (m, 1H), 1.42-1.34 (m, 2H), 1.25 (s, 9H). MS: M m/z=372.2 HPLC: 96%, (Condition-A).

후처리

  1. concentrationconcentrated in vacuo
  2. dissolutionthe residue was then dissolved in DCM (50 mL)
  3. washThe organic layer was washed with saturated NaHCO3 solution (15 mL) and brine (15 mL)
  4. customThe organic layer was then separated
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto obtain the crude product
  9. customThe crude material was purified via silica gel column chromatography
  10. washeluting with 1% MeOH in dichloromethane

출처 및 근거

ORD 기록
ord-577731232e1945eb8b755f45afb7bd17
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481532B2

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