Triethylamine → HCID 57786056, 화합물

HRID 1628909노트

반응식

HRID 1628909 반응식
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]3[C:17]([Cl:18])=[CH:16][C:15]([Cl:19])=[CH:14][C:13]=3[Cl:20])[N:7]([CH2:21][CH2:22][CH2:23]O)[C:6]=2[C:5]([C:25]([O:27][CH3:28])=[O:26])=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)(=O)C.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:25]([O:27][CH3:28])=[O:26])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:12]3[C:13]([Cl:20])=[CH:14][C:15]([Cl:19])=[CH:16][C:17]=3[Cl:18])[CH2:23][CH2:22][CH2:21][N:7]21

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 68761466Methyl 4-chloro-1-(3-hydroxypropyl)-2-[(2,4,6-trichlorophenyl)amino]-1H-benzimidazole-7-carboxylate

생성물 1

HCID 57786056HCID 57786056, 화합물수율 87.4%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of methyl 4-chloro-1-(3-hydroxypropyl)-2-[(2,4,6-trichlorophenyl)amino]-1H-benzimidazole-7-carboxylate (250 mg, 0.540 mmol) and triethylamine (0.376 mL, 2.70 mmol) in tetrahydrofuran (2.7 mL) was added methanesulfonyl chloride (0.171 mL, 2.16 mmol) at 0° C. The resultant mixture was stirred at room temperature for 1 hr and concentrated in vacuo. After N,N-dimethylformamide (5.4 mL) and potassium carbonate (746 mg, 5.40 mmol) were added to the residue, the resultant mixture was stirred at 80° C. for 1 hr, diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless solid (210 mg, 0.472 mmol, 87%).

후처리

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

출처 및 근거

ORD 기록
ord-8880f0df7f1043f5b17c8d11156a3e4a
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785460B2

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