1-Hydroxybenzotriazole → HCID 57874460、化合物

HRID 1093688

反応式

HRID 1093688 の反応式
[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11](=[O:16])[CH2:12][C:13]([OH:15])=O)[CH2:7][CH2:6]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[C:43]1([C:49]2[N:54]=[CH:53][C:52]([NH2:55])=[CH:51][CH:50]=2)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CN(C=O)C.CN(C1C=CN=CC=1)C.O>[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[O:4][CH:5]1[CH2:6][CH2:7][N:8]([C:11](=[O:16])[CH2:12][C:13]([NH:55][C:52]2[CH:53]=[N:54][C:49]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[CH:50][CH:51]=2)=[O:15])[CH2:9][CH2:10]1

参加物

8

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27628776-Phenylpyridin-3-amineHCID 57874403HCID 57874403、化合物

生成物 1

HCID 57874460HCID 57874460、化合物収率 53%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 3-[4-(2-chloro-phenoxy)-piperidin-1-yl]-3-oxo-propionic acid (0.08 g, 0.00027 mole) in DMF (3 mL) was added DMAP (0.049 g, 0.00040 mole), HOBt (0.043 g, 0.00032 mole) and EDCI.HCl (0.06 g, 0.00032 mole). After 2 minutes 6-phenyl-pyridin-3-ylamine (0.055 g, 0.00032 mole) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water and the product was extracted with ethyl acetate ethyl acetate. The organic layer was washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure to afford 0.0642 g (53%) of 3-[4-(2-chloro-phenoxy)-piperidin-1-yl]-3-oxo-N-(6-phenyl-pyridin-3-yl)-propionamide. LC-MS purity: 450.15 (M+1)+, 99.25%, 1H NMR (DMSO-d6): δ 10.4 (s, 1H), 8.8 (s, 1H), 8.2 (dd, 1H), 8.1-8.0 (m, 2H), 8.0-7.9 (m, 1H), 7.5-7.2 (m, 6H), 7.0-6.9 (m, 1H), 4.8-4.7 (m, 1H), 3.8-3.7 (m, 2H), 3.7-3.6 (s, 2H), 3.6-3.5 (m, 2H), 2.1-1.5 (m, 4H).

後処理

  1. extractionthe product was extracted with ethyl acetate ethyl acetate
  2. washThe organic layer was washed with brine solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-29c0be9450ca46059b41a909b6b04a31
出典データセット
uspto-grants-2012_03
特許番号
US08129376B2

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