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1,2-Dichloroethane → N-benzyl-1-(1-(4-chlorobenzyl)-7-methyl-1H-indole-2-carbonyl)piperidine-4-carboxamide

HRID 83681
ノート
印刷プレビュー

反応式

HRID 83681 の反応式
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[CH3:16])[CH:9]=[C:8]2[C:17](O)=[O:18])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH2:45]([NH:52][C:53]([CH:55]1[CH2:60][CH2:59][NH:58][CH2:57][CH2:56]1)=[O:54])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>CCOC(C)=O.CN(C=O)C>[CH2:45]([NH:52][C:53]([CH:55]1[CH2:60][CH2:59][N:58]([C:17]([C:8]2[N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:21][CH:20]=3)[C:15]3[C:10]([CH:9]=2)=[CH:11][CH:12]=[CH:13][C:14]=3[CH3:16])=[O:18])[CH2:57][CH2:56]1)=[O:54])[C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 3868064N-benzylpiperidine-4-carboxamideHCID 683797591-(4-chlorobenzyl)-7-methyl-1H-indole-2-carboxylic acid

生成物 1

HCID 66571684N-benzyl-1-(1-(4-chlorobenzyl)-7-methyl-1H-indole-2-carbonyl)piperidine-4-carboxamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

The following was added to sequentially to DMF (2 mL): 1-(4-chlorobenzyl)-7-methyl-1H-indole-2-carboxylic acid (50 mg, 0.167 mmol), DIPEA (0.10 mL, 0.584 mmol), EDC (38 mg, 0.200 mmol), and HOBT (31 mg, 0.200 mmol). This was allowed to stir for 30 min at rt, after which time the crude N-benzylpiperidine-4-carboxamide (˜36 mg, 0.20 mmol) was added. The reaction was stirred at rt for 18 h, at which time the reaction was diluted with 1:1 EtOAc:diethyl ether and washed with 10% aq. sodium carbonate (2×), dried over magnesium sulfate, and concentrated. The residue was purified via silica gel flash chromatography (20 g silica, 50% EtOAc/Hexanes) to afford the title compound as a white powder. (Yield: 39 mg, 0.078 mmol, 47%) 1H NMR (400 MHz, CDCl3) 7.50, 7.38-7.26, 7.18, 7.05-6.97, 6.81, 6.63, 5.72, 5.66-5.57, 4.70-3.89, 4.44, 2.86-2.66, 2.57, 2.32-2.23, 1.77

後処理

  1. stirringThe reaction was stirred at rt for 18 h, at which time the reaction
  2. washdiethyl ether and washed with 10% aq. sodium carbonate (2×)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified via silica gel flash chromatography (20 g silica, 50% EtOAc/Hexanes)

出典と根拠

ORDレコード
ord-add255bcb05444f6877328775a1193d3
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08846684B2

反応ノート

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