Potassium Carbonate → HCID 57786190, 화합물

HRID 1398982노트

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HRID 1398982 반응식
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]3[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[CH:13]=3)[N:7]([CH2:20][CH2:21][CH2:22][CH2:23]O)[C:6]=2[C:5]([CH:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[CH:4][CH:3]=1.CS(Cl)(=O)=O.C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.O>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:12]4[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[CH:13]=4)[CH2:23][CH2:22][CH2:21][CH2:20][N:7]3[C:6]=2[C:5]([CH:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 68772458HCID 68772458, 화합물

생성물 1

HCID 57786190HCID 57786190, 화합물수율 93.3%

시약·촉매·용매 2

HCID 962Water용매HCID 1049Pyridine용매

실험 절차

To a solution of 4-[4-chloro-2-[(3,5-dichlorophenyl)amino]-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butan-1-ol (Reference Example 42; 7.0 mg, 0.015 mmol) in pyridine (1.0 mL) was added methanesulfonyl chloride (0.050 mL, 0.064 mmol) dropwise at 0° C. The mixture was warmed to room temperature and stirred for 26 hr. Aqueous sodium bicarbonate was added and the mixture was extracted with ethyl acetate. Organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The resulting crude mesylate was dissolved in N,N-dimethylformamide (1.0 mL) and potassium carbonate (11 mg, 0.077 mmol) was added. The mixture was stirred at 80° C. for 16 hr. Water was added and the mixture was extracted with ethyl acetate. Organic layer was 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 5-20% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound (6.1 mg, 0.014 mmol, 93%) as a colorless amorphous.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washOrganic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. dissolutionThe resulting crude mesylate was dissolved in N,N-dimethylformamide (1.0 mL)
  6. stirringThe mixture was stirred at 80° C. for 16 hr
  7. extractionthe mixture was extracted with ethyl acetate
  8. washOrganic layer was washed with water and brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by flash chromatography on silica gel eluting with a 5-20% ethyl acetate/n-hexane gradient mixture
  12. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-e258c0b1fc4341fb82432905f54f41d8
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901141B2

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