Water → HCID 86655407, 화합물

HRID 2190480노트

반응식

HRID 2190480 반응식
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:13]=[C:14]([NH:19][C:20](=[O:33])[C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([C:30]#[N:31])([CH3:29])[CH3:28])[C:22]=4[Cl:32])[CH:15]=[CH:16][C:17]=3[F:18])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:34]1([C:37](Cl)=[O:38])[CH2:36][CH2:35]1.N1C=CC=CC=1.O>O1CCCC1.C(OCC)(=O)C>[Cl:32][C:22]1[C:23]([C:27]([C:30]#[N:31])([CH3:29])[CH3:28])=[CH:24][CH:25]=[CH:26][C:21]=1[C:20]([NH:19][C:14]1[CH:15]=[CH:16][C:17]([F:18])=[C:12]([O:11][C:9]2[CH:8]=[CH:7][C:5]3[N:6]=[C:2]([NH:1][C:37]([CH:34]4[CH2:36][CH2:35]4)=[O:38])[S:3][C:4]=3[CH:10]=2)[CH:13]=1)=[O:33]

참가 물질

7

반응물 4

HCID 962WaterHCID 1049PyridineHCID 77637Cyclopropanecarbonyl chlorideHCID 86655406N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]-4-fluorophenyl}-2-chloro-3-(1-cyano-1-methylethyl)benzamide

생성물 1

HCID 86655407HCID 86655407, 화합물수율 40.4%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]-4-fluorophenyl}-2-chloro-3-(1-cyano-1-methylethyl)benzamide (350 mg, 0.73 mmol) produced in Example A47(ii) in tetrahydrofuran (20 mL) were added cyclopropanecarbonyl chloride (114 mg, 1.09 mmol) and pyridine (86 mg, 1.09 mmol), and the mixture was stirred at room temperature for 30 min. Water (100 mL) and ethyl acetate (100 mL) were added to the reaction mixture, and the mixture was stirred for 30 min. The organic layer was separated, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=20/80→0/100), and triturated with ethyl acetate/hexane to give the title compound (162 mg, 40%) as a colorless solid.

후처리

  1. stirringthe mixture was stirred for 30 min
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=20/80→0/100)
  7. customtriturated with ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-78d75b5ffbe84736a4d0058a44bad5e0
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324395B2

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