1,1,1-Trifluoro-2,4-pentanedione → 1-[4-(3,4-dichloro-phenyl)-2-methyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-b]pyridin-3-yl]-2,2,2-trifluoro-ethanone

HRID 133492

반응식

HRID 133492 반응식
[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)=O.[F:20][C:21]([F:29])([F:28])[C:22](=[O:27])[CH2:23][C:24](=O)[CH3:25]>C(O)(=O)C.S(=O)(=O)(O)O>[Cl:19][C:14]1[CH:13]=[C:12]([C:10]2[C:23]([C:22](=[O:27])[C:21]([F:29])([F:28])[F:20])=[C:24]([CH3:25])[N:1]=[C:2]3[S:6][C:5]4[CH2:7][CH2:8][CH2:9][C:4]=4[C:3]=23)[CH:17]=[CH:16][C:15]=1[Cl:18]

참가 물질

5

반응물 2

HCID 739431,1,1-Trifluoro-2,4-pentanedioneHCID 283374393-(3,4-dichlorobenzoyl)-4H,5H,6H-cyclopenta[b]thiophen-2-amine

생성물 1

HCID 116976611-[4-(3,4-dichloro-phenyl)-2-methyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-b]pyridin-3-yl]-2,2,2-trifluoro-ethanone수율 14%

시약·촉매·용매 2

HCID 1118Sulfuric Acid촉매HCID 176Acetic Acid용매

반응 조건

온도
100 °C

실험 절차

To a stirred solution of 50 mg (0.16 mmol) (2-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-(3,4-dichloro-phenyl)-methanone in 2 ml acetic acid was added 0.020 ml (0.17 mmol) of 1,1,1-trifluoro-pentane-2,4-dione and one drop of sulfuric acid. The mixture was then stirred at 100° C. for 10 minutes in a microwave and then concentrated in vacuo. Flash chromatography (heptane/ethyl acetate 10:1) afforded 9 mg (14%) 1-[4-(3,4-dichloro-phenyl)-2-methyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-b]pyridin-3-yl]-2,2,2-trifluoro-ethanone as a yellow solid. ES-MS m/e (%): 430 (M+H+, 100).

후처리

  1. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-5dcb37703fe34f8d8adc151c065ecd36
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390903B2

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