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Sodium Iodide → 1-{3-[2-(1H-Imidazol-1-yl)ethoxy]phenyl}-3-(morpholin-4-ylcarbonyl)-1,4-dihydrothiochromeno[4,3-c]pyrazole 5,5-dioxide

HRID 1521861
ノート
印刷プレビュー

反応式

HRID 1521861 の反応式
[N:1]1([C:7]([C:9]2[C:10]3[CH2:28][S:27](=[O:30])(=[O:29])[C:26]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:11]=3[N:12]([C:14]3[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=3)[N:13]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl.Cl[CH2:41][CH2:42][N:43]1[CH:47]=[CH:46][N:45]=[CH:44]1>CN(C=O)C.O>[N:43]1([CH2:42][CH2:41][O:20][C:16]2[CH:15]=[C:14]([N:12]3[C:11]4[C:21]5[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=5[S:27](=[O:29])(=[O:30])[CH2:28][C:10]=4[C:9]([C:7]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[O:8])=[N:13]3)[CH:19]=[CH:18][CH:17]=2)[CH:47]=[CH:46][N:45]=[CH:44]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 27575031-(2-chloroethyl)-1H-imidazole hydrochlorideHCID 665789283-[3-(Morpholin-4-ylcarbonyl)-5,5-dioxidothiochromeno[4,3-c]pyrazol-1(4H)-yl]phenol

生成物 1

HCID 665809621-{3-[2-(1H-Imidazol-1-yl)ethoxy]phenyl}-3-(morpholin-4-ylcarbonyl)-1,4-dihydrothiochromeno[4,3-c]pyrazole 5,5-dioxide

試薬・触媒・溶媒

2
HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a suspension of 3-[3-(morpholin-4-ylcarbonyl)-5,5-dioxidothiochromeno[4,3-c]pyrazol-1(4H)-yl]phenol (206.5 mg; 0.49 mmol; 1 eq.), potassium carbonate (401.6 mg; 2.91 mmol; 5.99 eq.) and sodium iodide (11.7 mg; 0.08 mmol; 0.16 eq.) in DMF (4 ml) is added N-(2-chloroethyl)-imidazole hydrochloride (158.4 mg; 0.95 mmol; 1.95 eq.). The suspension is stirred at 80° C. 2 days then in the microwave at 120° C. for 30 min. The reaction mixture is diluted with water and the product is extracted with EtOAc. The combined organic layer is washed with water then with brine, dried over MgSO4 and the solvent removed under vacuum to afford a brown residue. After purification by flask chromatography (silica; DCM/MeOH 98/2 to 0/100), it affords the title compound as a fluffy yellow powder. 1H NMR (DMSO-d6): δ 8.07-7.98 (m, 1H), 7.73-7.55 (m, 3H), 7.55-7.44 (m, 1H), 7.28-7.13 (m, 3H), 7.09-7.00 (m, 1H), 6.93-6.83 (m, 2H), 4.10 (s, 2H), 4.44-4.22 (m, 4H), 4.00-3.87 (m, 2H), 3.75-3.55 (m, 6H). HPLC (max plot) 93.5%; Rt 2.48 min. MS (ESI+): 520.4.

後処理

  1. extractionthe product is extracted with EtOAc
  2. washThe combined organic layer is washed with water
  3. dry with materialwith brine, dried over MgSO4
  4. customthe solvent removed under vacuum
  5. customto afford a brown residue
  6. customAfter purification by flask chromatography (silica; DCM/MeOH 98/2 to 0/100), it

出典と根拠

ORDレコード
ord-4de4d34a6f0a4806b02ba947c6fcd329
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09073940B2

反応ノート

読み込み中…

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