1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67386157、化合物

HRID 1898543ノート

反応式

HRID 1898543 の反応式
[O:1]([C:8]1[N:9]=[C:10]2[C:16]([C:17](O)=[O:18])=[CH:15][N:14]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:11]2=[N:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)CCCN=C=NCC.[NH2:39][C@H:40]([CH:48]([CH3:50])[CH3:49])[C:41]([N:43]1[CH2:47][CH2:46][CH2:45][CH2:44]1)=[O:42]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:49][CH:48]([CH3:50])[C@@H:40]([NH:39][C:17]([C:16]1[C:10]2[C:11](=[N:12][CH:13]=[C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[N:9]=2)[N:14]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:26])([CH3:27])[CH3:25])[CH:15]=1)=[O:18])[C:41]([N:43]1[CH2:47][CH2:46][CH2:45][CH2:44]1)=[O:42]

参加物

6

反応物 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 40459151HCID 40459151、化合物HCID 58522244HCID 58522244、化合物

生成物 1

HCID 67386157HCID 67386157、化合物

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 2-phenoxy-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (0.10 g, 0.26 mmol), 4-dimethylaminopyridine (0.048 g, 0.39 mmol) and (3-dimethylamino-propyl)-ethyl-carbodiimide (0.075 g, 0.39 mmol) in CH2Cl2 (2 mL) was added (R)-2-amino-3-methyl-1-pyrrolidin-1-yl-butan-1-one (0.066 g, 0.39 mmol) in CH2Cl2 (0.5 mL). The reaction mixture was stirred at room temperature overnight, then quenched with water and extracted with ethyl acetate (3×). The organic layer was washed with water and saturated aqueous NaCl solution and dried over MgSO4, filtered and concentrated. The residue was purified by SiO2 column chromatography (0-100% EtOAc/hexanes) to afford 2-phenoxy-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-methyl-1-(pyrrolidine-1-carbonyl)-propyl]-amide as a yellow oil.

後処理

  1. customquenched with water
  2. extractionextracted with ethyl acetate (3×)
  3. washThe organic layer was washed with water and saturated aqueous NaCl solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by SiO2 column chromatography (0-100% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-e8c2b9733817488b930aff2f4b6798ff
出典データセット
uspto-grants-2013_08
特許番号
US08518945B2

反応ノート

読み込み中…