1,2-Dichloroethane → (1-(4-fluorobenzyl)-1H-indol-2-yl)(4-(piperidine-1-carbonyl)piperidin-1-yl)methanone

HRID 83607

反応式

HRID 83607 の反応式
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16](O)=[O:17])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[N:44]1([C:50]([CH:52]2[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]2)=[O:51])[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]1>C(OCC)C.C(OCC)(=O)C.CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:55]2[CH2:54][CH2:53][CH:52]([C:50]([N:44]3[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]3)=[O:51])[CH2:57][CH2:56]2)=[O:17])=[CH:19][CH:20]=1

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27946881-(Piperidin-4-ylcarbonyl)piperidineHCID 186270691-(4-fluorobenzyl)-1H-indole-2-carboxylic acid

生成物 1

HCID 66571097(1-(4-fluorobenzyl)-1H-indol-2-yl)(4-(piperidine-1-carbonyl)piperidin-1-yl)methanone収率 34.8%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 21584169Diethylether ethylacetate溶媒

実験手順

The following was added sequentially to anhydrous DMF (2 mL): 1-(4-fluorobenzyl)-1H-indole-2-carboxylic acid (50 mg, 0.186 mmol), Hunig's Base (0.065 ml, 0.371 mmol), EDC (46.3 mg, 0.241 mmol), HOBT (37.0 mg, 0.241 mmol), and piperidin-1-yl(piperidin-4-yl)methanone (36.4 mg, 0.186 mmol). The solution was allowed to stir at room temperature for 24 h. At this time, a 1:1 solution of diethylether/ethyl acetate (5 mL) was added, and this was washed with aqueous 10% Na2CO3 (3×2 mL). The extract was then dried with anhydrous MgSO4, filtered, and the filtrate was concentrated in vacuo. The crude residue was purified by column chromatography (20 g silica, 80% EtOAc/Hex) to provide 29 mg of the title compound.

後処理

  1. washthis was washed with aqueous 10% Na2CO3 (3×2 mL)
  2. dry with materialThe extract was then dried with anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe crude residue was purified by column chromatography (20 g silica, 80% EtOAc/Hex)

出典と根拠

ORDレコード
ord-7bc0b766889840ecb2fa528f206d1e58
出典データセット
uspto-grants-2014_09
特許番号
US08846684B2

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