1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-[7-(benzyloxy)-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl]-4-hydroxy-1,1-dipropyl-2(1H)-naphthalenone

HRID 494447노트

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HRID 494447 반응식
[NH2:1][S:2]([C:5]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]=[CH:7][C:6]=1[NH:19][C:20]([C:22]1[C:31](=[O:32])[C:30]([CH2:36][CH2:37][CH3:38])([CH2:33][CH2:34][CH3:35])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]=1[OH:39])=O)(=[O:4])=[O:3].N12CCCN=C1CCCCC2>N1C=CC=CC=1>[CH2:12]([O:11][C:9]1[CH:8]=[CH:7][C:6]2[NH:19][C:20]([C:22]3[C:31](=[O:32])[C:30]([CH2:33][CH2:34][CH3:35])([CH2:36][CH2:37][CH3:38])[C:29]4[C:24]([C:23]=3[OH:39])=[CH:25][CH:26]=[CH:27][CH:28]=4)=[N:1][S:2](=[O:4])(=[O:3])[C:5]=2[CH:10]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

4

반응물 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68871690N-[2-(aminosulfonyl)-4-(benzyloxy)phenyl]-1-hydroxy-3-oxo-4,4-dipropyl-3,4-dihydro-2-naphthalenecarboxamide

생성물 1

HCID 1363756003-[7-(benzyloxy)-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl]-4-hydroxy-1,1-dipropyl-2(1H)-naphthalenone수율 38%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
140 °C

실험 절차

A solution of the compound of Example 2E (300 mg, 0.547 mmol) in anhydrous pyridine (5.2 mL) was treated with 1,8diazabicyclo[5.4.0]undec-7-ene (82 μL, 0.55 mmol) and stirred at 140° C. for 18 hours, cooled to 25° C. and the pyridine removed by short path distillation under high vacuum (50° C./0.3 mm Hg). A solution of the residue in ethyl acetate was washed with water (2×) and saturated sodium chloride solution, dried (Na2SO4), filtered and concentrated in vacuo. The residue was chromatographed on silica gel, eluting with ethyl acetate in hexane to give the title compound (110 mg, 38%). 1H NMR (300 MHz, DMSO-d6): δ 8.11 (d, J=7.72 Hz, 1 H), 7.64 (m, 1 H), 7.41 (m, 8 H), 5.21 (s, 2 H), 2.14 (m, 2 H), 1.83 (m, 2 H), 0.87 (m, 2 H), 0.64 (m, 8 H).

후처리

  1. temperaturecooled to 25° C.
  2. customthe pyridine removed by short path distillation under high vacuum (50° C./0.3 mm Hg)
  3. washA solution of the residue in ethyl acetate was washed with water (2×) and saturated sodium chloride solution
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel
  8. washeluting with ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-af52fb6d7ac64b2c80902317822bdeb4
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538105B2

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