Hydrazine hydrate (1:1) → 1'-(3-aminopropyl)spiro[furo[2,3-f]-[1,3]benzodioxole-7,3'-indol]-2'(1'H)-one

HRID 425711노트

반응식

HRID 425711 반응식
[O:1]=[C:2]1[C:10]2([C:14]3=[CH:15][C:16]4[O:20][CH2:19][O:18][C:17]=4[CH:21]=[C:13]3[O:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:22][CH2:23][CH2:24][N:25]1C(=O)C2C(=CC=CC=2)C1=O.O.NN>C(O)C>[NH2:25][CH2:24][CH2:23][CH2:22][N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10]2([C:14]3=[CH:15][C:16]4[O:20][CH2:19][O:18][C:17]=4[CH:21]=[C:13]3[O:12][CH2:11]2)[C:2]1=[O:1]

참가 물질

4

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 119980722-[3-(2'-oxospiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-1'(2'H)-yl)propyl]-1H-isoindole-1,3(2H)-dione

생성물 1

HCID 119998911'-(3-aminopropyl)spiro[furo[2,3-f]-[1,3]benzodioxole-7,3'-indol]-2'(1'H)-one수율 108.7%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 2-[3-(2′-oxospiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-1′(2′H)-yl)propyl]-1H-isoindole-1,3(2H)-dione (3.20 g, 6.80 mmol) in ethanol (70.0 mL) was added hydrazine monohydrate (1.87 g, 37.0 mmol). The mixture was stirred at ambient temperature for 4 h. The solvent was removed under reduced pressure and the residue was re-dissolved in ethyl acetate. The solution was washed with sodium bicarbonate and brine solution, dried over MgSO4 and filtered. The filtrate was concentrated in vacuo to dryness. The residue was crystallized from hexane to yield the title compound (2.50 g) in 75% yield: 1H NMR (300 MHz, CDCl3) δ 7.31-7.24 (m, 1H), 7.16-7.14 (m, 1H), 7.06-7.01 (m, 1H), 6.94-6.91 (m, 1H), 6.48 (s, 1H), 6.10 (s, 1H), 5.82 (m, 2H), 4.90-4.87 (m, 1H), 4.61 (d, 1H), 3.98-3.71 (m, 2H), 2.77-2.73 (m, 2H), 1.97 (br, 2H), 1.84-1.81 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 177.8, 155.9 , 148.9, 142.3, 142.2, 132.4, 129.0, 124.0, 123.4, 119.4, 108.7, 103.0, 101.5, 93.6, 80.5, 58.2, 38.8, 37.5, 30.6; MS (ES+) m/z 339.3 (M+1).

후처리

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was re-dissolved in ethyl acetate
  3. washThe solution was washed with sodium bicarbonate and brine solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo to dryness
  7. customThe residue was crystallized from hexane

출처 및 근거

ORD 기록
ord-0cd2e776cac74f76ac95a4d4a1979b81
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106087B2

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