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Potassium Carbonate → US10023592, Example 287

HRID 518497
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HRID 518497 반응식
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])=[CH:8][C:7]=2[C:17]2[CH:18]=[C:19]([OH:25])[C:20](=[O:24])[N:21]([CH3:23])[CH:22]=2)[CH2:3][CH2:2]1.Cl[C:27]([F:32])([F:31])C([O-])=O.[Na+].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])=[CH:8][C:7]=2[C:17]2[CH:18]=[C:19]([O:25][CH:27]([F:32])[F:31])[C:20](=[O:24])[N:21]([CH3:23])[CH:22]=2)[CH2:3][CH2:2]1
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5

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HCID 11430Potassium CarbonateHCID 2734985Sodium chlorodifluoroacetateHCID 1180221155-[2-(Cyclopropylmethoxy)-5-ethylsulfonylphenyl]-3-hydroxy-1-methylpyridin-2-one

생성물 1

HCID 118022452US10023592, Example 287수율 28%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

A mixture of 5-[2-(cyclopropylmethoxy)-5-ethylsulfonylphenyl]-3-hydroxy-1-methylpyridin-2-one (50 mg, 0.14 mmol), sodium chlorodifluoroacetate (252 mg, 1.65 mmol), K2CO3 (70 mg, 0.51 mmol) in dioxane (4 mL) was stirred at 100° C. for 18 h. After the mixture was filtered, the filtrate was concentrated in vacuo. The residue was purified by prep-HPLC to give the title compound (16 mg, 28%) as a light pink solid. 1H NMR (CDCl3, 400 MHz) δ 7.84 (m, 1H) 7.77 (d, J=2.4 Hz, 1H) 7.63 (d, J=2.4 Hz, 1H) 7.49 (d, J=2.4 Hz, 1H) 7.04 (m, 1H) 3.95 (m, 2H) 3.69 (s, 3H) 3.13 (m, 3H) 1.33-1.26 (m, 4H) 0.72-0.67 (m, 2H) 0.39-0.36 (m, 2H). LCMS (M+H)+=414.

후처리

  1. filtrationAfter the mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by prep-HPLC

출처 및 근거

ORD 기록
ord-49af92a121a042c5a6fe239e4230b3b1
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09115114B2

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