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Sodium methanesulfinate → 10-Chloro-7-(1-ethylpropyl)-1-[3-methyl-5-(methylsulfonyl)pyridin-2-yl]-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazole

HRID 1399229
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HRID 1399229 반응식
Br[C:2]1[CH:3]=[C:4]([CH3:28])[C:5]([N:8]2[C:14]3=[N:15][C:16]4[C:21]([Cl:22])=[CH:20][CH:19]=[C:18]([CH:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[C:17]=4[N:13]3[CH2:12][CH2:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.[CH3:29][S:30]([O-:32])=[O:31].[Na+]>CN1CCCC1=O.C(OCC)(=O)C.[Cu]I>[Cl:22][C:21]1[C:16]2[N:15]=[C:14]3[N:8]([C:5]4[C:4]([CH3:28])=[CH:3][C:2]([S:30]([CH3:29])(=[O:32])=[O:31])=[CH:7][N:6]=4)[CH2:9][CH2:10][CH2:11][CH2:12][N:13]3[C:17]=2[C:18]([CH:23]([CH2:26][CH3:27])[CH2:24][CH3:25])=[CH:19][CH:20]=1
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참가 물질

6

반응물 2

HCID 2733271Sodium methanesulfinateHCID 577864001-(5-bromo-3-methylpyridin-2-yl)-10-chloro-7-(1-ethylpropyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazole

생성물 1

HCID 5778610110-Chloro-7-(1-ethylpropyl)-1-[3-methyl-5-(methylsulfonyl)pyridin-2-yl]-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazole수율 36.2%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 8857Ethyl Acetate용매
HCID 13387N-methyl-2-pyrrolidone용매

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온도
180 °C

실험 절차

A mixture of 1-(5-bromo-3-methylpyridin-2-yl)-10-chloro-7-(1-ethylpropyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazole (463 mg, 0.216 mmol), 1.0 sodium methanesulfinate (66 mg, 0.648 mmol) and copper(I) iodide (123 mg, 0.648 mmol) in 1-methyl-2-pyrrolidinone (1.0 mL) was heated under microwave irradiation at 180° C. for 1 hr. After cooling, the mixture was diluted with ethyl acetate, filtered through a pad of celite, washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture followed by recrystallization from ethyl acetate/n-hexane to afford the title compound (36 mg, 36%) as a colorless solid.

후처리

  1. temperatureAfter cooling
  2. filtrationfiltered through a pad of celite
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture
  7. customfollowed by recrystallization from ethyl acetate/n-hexane

출처 및 근거

ORD 기록
ord-231bcd94de56496eb2c46c0c44e42758
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08901141B2

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