Pyridine → HCID 86644710, 화합물

HRID 1097536노트

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HRID 1097536 반응식
[NH2:1][C:2]1[S:3][C:4]2[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([O:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[C:18]([NH:23][C:24](=[O:36])[CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=4)[CH:17]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1.N1C=CC=CC=1.[CH:43]1([C:46](Cl)=[O:47])[CH2:45][CH2:44]1>O1CCCC1.C(OCC)(=O)C>[CH:43]1([C:46]([NH:1][C:2]2[S:3][C:4]3[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([O:15][C:16]4[CH:21]=[CH:20][C:19]([F:22])=[C:18]([NH:23][C:24](=[O:36])[CH2:25][C:26]5[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:34])([F:35])[F:33])[CH:27]=5)[CH:17]=4)[CH:8]=[CH:7][C:5]=3[N:6]=2)=[O:47])[CH2:45][CH2:44]1

참가 물질

6

반응물 3

HCID 1049PyridineHCID 77637Cyclopropanecarbonyl chlorideHCID 86644709HCID 86644709, 화합물

생성물 1

HCID 86644710HCID 86644710, 화합물수율 80%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of methyl 2-amino-6-[4-fluoro-3-({[3-(trifluoromethyl)phenyl]acetyl}amino)phenoxy]-1,3-benzothiazole-7-carboxylate (2.50 mg, 4.81 mmol) in tetrahydrofuran (20 mL) were added pyridine (770 μL, 9.62 mmol) and cyclopropanecarbonyl chloride (790 μL, 8.66 mmol), and the mixture was stirred at room temperature for 12 hr. The reaction mixture was diluted with ethyl acetate (80 mL), washed successively with saturated aqueous sodium hydrogen carbonate solution (50 ml) and saturated brine (50 mL), and the organic layer was dried over anhydrous magnesium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=40/60→80/20), and a fraction containing the object product was concentrated under reduced pressure. The obtained pale-yellow residue was recrystallized from ethyl acetate/n-hexane (3/2) to give the title compound (2.25 g, 80%) as a white powder.

후처리

  1. washwashed successively with saturated aqueous sodium hydrogen carbonate solution (50 ml) and saturated brine (50 mL)
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationInsoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=40/60→80/20)
  6. additiona fraction containing the object product
  7. concentrationwas concentrated under reduced pressure
  8. customThe obtained pale-yellow residue was recrystallized from ethyl acetate/n-hexane (3/2)

출처 및 근거

ORD 기록
ord-7fe9a3a29c6e44acbc8ad749577afb6b
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143258B2

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