1,2-Dichloroethane → 1-(1-(4-chlorobenzyl)-1H-benzo[d]imidazole-2-carbonyl)-N-(2-(pyridin-4-yl)ethyl)piperidine-4-carboxamide

HRID 83653

反応式

HRID 83653 の反応式
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24](O)=[O:25])[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1.C(Cl)CCl.ON1C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[N:52]1[CH:57]=[CH:56][C:55]([CH2:58][CH2:59][NH2:60])=[CH:54][CH:53]=1>C(Cl)Cl.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]([NH:60][CH2:59][CH2:58][C:55]3[CH:56]=[CH:57][N:52]=[CH:53][CH:54]=3)=[O:25])[CH2:20][CH2:19]2)=[O:17])=[CH:27][CH:28]=1

参加物

9

反応物 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 832754-PyridineethanamineHCID 68380045HCID 68380045、化合物

生成物 1

HCID 665715191-(1-(4-chlorobenzyl)-1H-benzo[d]imidazole-2-carbonyl)-N-(2-(pyridin-4-yl)ethyl)piperidine-4-carboxamide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1-(1-(4-chlorobenzyl)-1H-benzo[d]imidazole-2-carbonyl)piperidine-4-carboxylic acid (50 mg, 0.126 mmol), EDC (48.2 mg, 0.251 mmol), and 1-hydroxybenzotriazole (34.0 mg, 0.251 mmol) were dissolved in DCM (Volume: 2.0 mL). The reaction was allowed to stir for 10 minutes before the addition of Hunig's Base (0.044 mL, 0.251 mmol) and 2-(pyridin-4-yl)ethanamine (0.030 mL, 0.251 mmol). The reaction was allowed to stir overnight. The reaction was diluted with water and ethyl acetate. The organic layer was washed with saturated sodium bicarbonate and saturated sodium chloride. The ethyl acetate layer was dried over magnesium sulfate, filtered and concentrated. The crude material was triturated in diethyl ether/ethyl acetate to obtain white solid. 1H-NMR (500 MHz, DMSO-d6) 8.47-8.43, 7.93, 7.74, 7.61, 7.39, 7.35-7.24, 7.21, 5.55, 4.45, 3.98, 3.33-3.28, 3.04, 2.87, 2.73, 2.40-2.31, 1.74, 1.58-1.32

後処理

  1. washThe organic layer was washed with saturated sodium bicarbonate and saturated sodium chloride
  2. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was triturated in diethyl ether/ethyl acetate
  6. customto obtain white solid

出典と根拠

ORDレコード
ord-9b19dee1017449189f94044d46d2e729
出典データセット
uspto-grants-2014_09
特許番号
US08846684B2

関連ノート

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