Methanesulfonyl chloride → HCID 57785826, 화합물

HRID 1628612노트

반응식

HRID 1628612 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:13]([CH2:14][CH2:15]O)[C:12]3[C:17]([CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:18][CH:19]=[C:20]([Cl:21])[C:11]=3[N:10]=2)=[C:4]([Cl:27])[CH:3]=1.CS(Cl)(=O)=O>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]3=[N:10][C:11]4[C:20]([Cl:21])=[CH:19][CH:18]=[C:17]([CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[C:12]=4[N:13]3[CH2:14][CH2:15]2)=[C:4]([Cl:27])[CH:3]=1

참가 물질

4

반응물 2

HCID 31297Methanesulfonyl chlorideHCID 68767091HCID 68767091, 화합물

생성물 1

HCID 57785826HCID 57785826, 화합물수율 85%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of 2-[2-[(4-bromo-2-chlorophenyl)amino]-4-chloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]ethanol (Reference Example 23; 1.19 g, 2.53 mmol) in pyridine (6.0 mL) was added methanesulfonyl chloride (979 μL, 12.65 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1.5 hr. The reaction mixture was quenched with saturated aqueous sodium hydrogen carbonate at 0° C. and extracted with ethyl acetate (×3). The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 0-15% ethyl acetate/n-hexane gradient mixture to give a solid. The resulting solid was recrystallized from n-hexane to give the title compound as a colorless powder (975.2 mg, 2.15 mmol, 85%).

후처리

  1. customThe reaction mixture was quenched with saturated aqueous sodium hydrogen carbonate at 0° C.
  2. extractionextracted with ethyl acetate (×3)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with a 0-15% ethyl acetate/n-hexane gradient mixture
  9. customto give a solid
  10. customThe resulting solid was recrystallized from n-hexane

출처 및 근거

ORD 기록
ord-4628fcc33c8f472896f1c59ada9631be
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785460B2

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