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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-(5-phenyl-pyridin-2-yl)-propionamide

HRID 1665698
ノート
印刷プレビュー

反応式

HRID 1665698 の反応式
[Br:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:17])[CH2:13][C:14]([OH:16])=O)[CH2:8][CH2:7]1)=[O:5].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[C:43]1([C:49]2[CH:50]=[CH:51][C:52]([NH2:55])=[N:53][CH:54]=2)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[Br:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[C:4]([N:6]1[CH2:7][CH2:8][N:9]([C:12](=[O:17])[CH2:13][C:14]([NH:55][C:52]2[CH:51]=[CH:50][C:49]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[CH:54][N:53]=2)=[O:16])[CH2:10][CH2:11]1)=[O:5]
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 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 1050975-Phenyl-2-pyridinamineHCID 578758013-[4-(2-Bromo-benzoyl)-piperazin-1-yl]-3-oxo-propionic acid

生成物 1

HCID 578758043-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-(5-phenyl-pyridin-2-yl)-propionamide収率 27.1%

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

DMAP (137 mg, 1.1 mmol) was added to 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-propionic acid (200 mg, 0.56 mmol) in DMF (2 mL) followed by EDCI (129 mg, 0.67 mmol) and HOBT (91 mg, 0.67 mmol). After 2 minutes, 5-phenyl-pyridin-2-ylamine (115 mg, 0.67 mmol) was added and stirring was continued at room temperature overnight. Cold water was then added and it was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure to afford 77 mg (27% yield) of 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-(5-phenyl-pyridin-2-yl)-propionamide. LC/MS [M+H]+: 507.1, 97.03%. 1H NMR (300 MHz, DMSO-d6): δ 10.8 (d, 1H), 8.7-8.6 (bs, 1H), 8.2-8.06 (m, 2H), 7.76-7.64 (m, 3H), 7.54-7.34 (m, 6H), 3.8-3.4 (m, 8H), 3.24-3.1 (m, 2H).

後処理

  1. waitwas continued at room temperature overnight
  2. extractionit was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-0791615c75564be287c974e56bd6e033
出典データセット
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08039463B2

反応ノート

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