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 494447ノート

反応式

HRID 494447 の反応式
[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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
140 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-af52fb6d7ac64b2c80902317822bdeb4
出典データセット
uspto-grants-2009_05
特許番号
US07538105B2

反応ノート

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