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

HRID 83681

반응식

HRID 83681 반응식
[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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-add255bcb05444f6877328775a1193d3
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846684B2

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