(2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-thiophen-2-yl-methanone → cyclopropyl-(2-methyl-4-thiophen-2-yl-6,7-dihydro-5H-cyclopenta[4.5]thieno[2,3-b]pyridin-3-yl)-methanone

HRID 133529

반응식

HRID 133529 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[S:13][CH:14]=[CH:15][CH:16]=1)=O.[CH:17]1([C:20](=[O:25])[CH2:21][C:22](=O)[CH3:23])[CH2:19][CH2:18]1>C(O)(=O)C.S(=O)(=O)(O)O>[CH:17]1([C:20]([C:21]2[C:10]([C:12]3[S:13][CH:14]=[CH:15][CH:16]=3)=[C:3]3[C:4]4[CH2:9][CH2:8][CH2:7][C:5]=4[S:6][C:2]3=[N:1][C:22]=2[CH3:23])=[O:25])[CH2:19][CH2:18]1

참가 물질

5

반응물 2

HCID 9899694(2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-thiophen-2-yl-methanoneHCID 110188691-Cyclopropyl-butane-1,3-dione

생성물 1

HCID 11702848cyclopropyl-(2-methyl-4-thiophen-2-yl-6,7-dihydro-5H-cyclopenta[4.5]thieno[2,3-b]pyridin-3-yl)-methanone수율 19%

시약·촉매·용매 2

HCID 1118Sulfuric Acid촉매HCID 176Acetic Acid용매

반응 조건

온도
100 °C

실험 절차

To a stirred solution of 60 mg (0.24 mmol) (2-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-thiophen-2-yl-methanone) (the preparation of which is described in example 2) in 2 ml acetic acid was added 40 mg (0.32 mmol) of 1-cyclopropyl-butane-1,3-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. Preparative HPLC (30% CH3CN/H20) afforded 15 mg (19%) cyclopropyl-(2-methyl-4-thiophen-2-yl-6,7-dihydro-5H-cyclopenta[4.5]thieno[2,3-b]pyridin-3-yl)-methanone as a light brown oil. ES-MS m/e (%): 340 (M+H+, 100).

후처리

  1. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d2dc0072d49e451f839ba50dedf64c0d
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390903B2

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