Triethylamine → HCID 57786371, 화합물

HRID 1628912노트

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HRID 1628912 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]([O:19][CH3:20])=[CH:14][C:13]=3[Cl:21])[N:7]([CH2:22][CH2:23][CH2:24]O)[C:6]=2[C:5]([C:26]([O:28][CH3:29])=[O:27])=[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:26]([O:28][CH3:29])=[O:27])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:12]3[C:13]([Cl:21])=[CH:14][C:15]([O:19][CH3:20])=[CH:16][C:17]=3[Cl:18])[CH2:24][CH2:23][CH2:22][N:7]21

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 68761403HCID 68761403, 화합물

생성물 1

HCID 57786371HCID 57786371, 화합물수율 86%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of methyl 4-chloro-2-[(2,6-dichloro-4-methoxyphenyl)amino]-1-(3-hydroxypropyl)-1H-benzimidazole-7-carboxylate (215 mg, 0.469 mmol) and triethylamine (0.327 mL, 2.35 mmol) in tetrahydrofuran (4.7 mL) was added methanesulfonyl chloride (0.148 mL, 1.87 mmol) at 0° C. The resultant mixture was stirred at room temperature for 30 min and concentrated in vacuo. After N,N-dimethylformamide (4.7 mL) and potassium carbonate (648 mg, 4.69 mmol) were added to the residue, the resultant mixture was stirred at 80° C. for 30 min, 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 20-50% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless solid (177 mg, 0.401 mmol, 86%).

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 20-50% ethyl acetate/n-hexane gradient mixture

출처 및 근거

ORD 기록
ord-88e014cf83244ffeafa089a7d93ea31a
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785460B2

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