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Chlorosuccinimide → (2-Chloro-5-phenyl-thiophen-3-yl)-(4,4-difluoro-azepan-1-yl)-methanone

HRID 2068662
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HRID 2068662 반응식
[F:1][C:2]1([F:22])[CH2:8][CH2:7][CH2:6][N:5]([C:9]([C:11]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:13][CH:12]=2)=[O:10])[CH2:4][CH2:3]1.[Cl:23]N1C(=O)CCC1=O>C(O)(=O)C.C(#N)C.O>[Cl:23][C:12]1[S:13][C:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:15][C:11]=1[C:9]([N:5]1[CH2:6][CH2:7][CH2:8][C:2]([F:1])([F:22])[CH2:3][CH2:4]1)=[O:10]
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참가 물질

6

반응물 2

HCID 31398ChlorosuccinimideHCID 44226682(4,4-Difluoro-azepan-1-yl)-(5-phenyl-thiophen-3-yl)-methanone

생성물 1

HCID 44226681(2-Chloro-5-phenyl-thiophen-3-yl)-(4,4-difluoro-azepan-1-yl)-methanone수율 25.5%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매
HCID 6342
Acetonitrile
용매

실험 절차

(4,4-Difluoro-azepan-1-yl)-(5-phenyl-thiophen-3-yl)-methanone (0.104 g, 0.33 mmol) and N-chlorosuccinimide (0.445 g, 0.33 mmol) in acetic acid (2 mL) were heated by microwave irradiation to 140° C. for 4 minutes. The mixture was diluted with acetonitrile and water and purified by HPLC, eluting with 10%-98% acetonitrile in water (0.1% formic acid). The fractions containing the desired product were evaporated to give the title compound as a gum (0.03 g). LCMS m/z 356.13 [M+H]+ R.T.=12.26 min (Analytical Method 2).

후처리

  1. custompurified by HPLC
  2. washeluting with 10%-98% acetonitrile in water (0.1% formic acid)
  3. additionThe fractions containing the desired product
  4. customwere evaporated

출처 및 근거

ORD 기록
ord-bbf8b46536144e45886f56358c56ce37
출처 데이터셋
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08299063B2

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