Water → N-(3-{[2-(acetylamino)-1,3-benzothiazol-6-yl]oxy}phenyl)-3-(1-cyanocyclopropyl)benzamide

HRID 2190449노트

반응식

HRID 2190449 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:18][C:19](=[O:31])[C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]5([C:29]#[N:30])[CH2:28][CH2:27]5)[CH:21]=4)[CH:15]=[CH:16][CH:17]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1.[C:32](Cl)(=[O:34])[CH3:33].C(N(CC)CC)C.O>O1CCCC1.C(OCC)(=O)C>[C:32]([NH:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:13]=[C:14]([NH:18][C:19](=[O:31])[C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]5([C:29]#[N:30])[CH2:27][CH2:28]5)[CH:21]=4)[CH:15]=[CH:16][CH:17]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1)(=[O:34])[CH3:33]

참가 물질

7

반응물 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86655364N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]phenyl}-3-(1-cyanocyclopropyl)benzamide

생성물 1

HCID 86655391N-(3-{[2-(acetylamino)-1,3-benzothiazol-6-yl]oxy}phenyl)-3-(1-cyanocyclopropyl)benzamide수율 69%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]phenyl}-3-(1-cyanocyclopropyl)benzamide (200 mg, 0.47 mmol) produced in Example A15(iii) in tetrahydrofuran (20 mL) were added acetyl chloride (0.3 mL, 4.22 mmol) and triethylamine (1.0 mL, 7.18 mmol), and the mixture was stirred at room temperature for 10 min. To the reaction mixture were added water (200 mL) and ethyl acetate (200 mL) 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 (151 mg, 69%) 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-99f6857670d84797a5a7d91eabf5ebeb
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324395B2

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