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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
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HRID 1521861 반응식
[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
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참가 물질

7

반응물 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

생성물 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

시약·촉매·용매

2
HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4de4d34a6f0a4806b02ba947c6fcd329
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09073940B2

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