1,2-Dichloroethane → N-cyclopropyl-N-{1-[2-{3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)propionyl]piperidin-4-yl}-propionamide

HRID 333422ノート

反応式

HRID 333422 の反応式
[CH:1]1([N:4]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[C:5](=[O:8])[CH2:6][CH3:7])[CH2:3][CH2:2]1.[NH:15]1[CH:19]=[C:18]([CH2:20][CH2:21][NH:22][C:23](=[O:38])[NH:24][CH:25]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)[C:26](O)=[O:27])[N:17]=[CH:16]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[CH:1]1([N:4]([CH:9]2[CH2:14][CH2:13][N:12]([C:26](=[O:27])[CH:25]([NH:24][C:23]([NH:22][CH2:21][CH2:20][C:18]3[N:17]=[CH:16][NH:15][CH:19]=3)=[O:38])[CH2:29][C:30]3[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=3)[CH2:11][CH2:10]2)[C:5](=[O:8])[CH2:6][CH3:7])[CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 12050271N-cyclopropyl-N-piperidin-4-ylpropionamideHCID 178490381HCID 178490381、化合物

生成物 1

HCID 178459999N-cyclopropyl-N-{1-[2-{3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)propionyl]piperidin-4-yl}-propionamide収率 8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

100 mg (0.51 mmol) of N-cyclopropyl-N-piperidin-4-ylpropionamide, 170 mg (0.51 mmol) of 2-{3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)propanoic acid (cf. preparation 2-3), 108 mg (0.56 mmol) of EDC and 76 mg (0.56 mmol) of HOBT are dissolved in 5 mL of DMF under nitrogen. The mixture is stirred at room temperature overnight, and the solution is then washed with aqueous 5% citric acid solution and extracted with ethyl acetate. The organic phase is washed with aqueous 1N NaOH solution and then dried and evaporated. The crude product obtained is purified by preparative HPLC (conditions cf. page 38). 2 mg of N-cyclopropyl-N-{1-[2-{3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)propionyl]piperidin-4-yl}-propionamide are obtained in a yield of 8%.

後処理

  1. washthe solution is then washed with aqueous 5% citric acid solution
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with aqueous 1N NaOH solution
  4. customdried
  5. customevaporated
  6. customThe crude product obtained
  7. customis purified by preparative HPLC (conditions cf. page 38)

出典と根拠

ORDレコード
ord-c1cf3dab7f384f2c99ac67fc06b84656
出典データセット
uspto-grants-2014_11
特許番号
US08877968B2

反応ノート

読み込み中…